Process for the preparation of 2-hydroxy-4-phenyl-3,4-dihydro-2H-chromen-6-yl-methanol and (R)-feso-deacyl

Process for the preparation of 2-hydroxy-4-phenyl-3,4-dihydro-2H-chromen-6-yl-methanol of formula (I),

• comprising:
• a. silylating 4-hydroxymethylphenol of formula (A)
• with a silylating agent to obtain a bis-silylated compound of formula (B)
• wherein PG is a silylated protective group;
• b. selectively deprotecting the phenolic hydroxyl of the bis-silylated compound of formula (B) to obtain a mono-silylated compound of formula (C)
• c. reacting the compound of formula (C) with trans-cinnamaldehyde and a cyclic secondary amine of formula (F)
• wherein
• R4 and R5 are equal or different from each other and are hydrogen, C1-C6 alkyl or aryl and n varies between 1 and 4;
• W is (CH2)m with m varying between 0 and 1, NR6 (with R6=C1-C6 alkyl or aryl), O or S;
• to obtain a compound of formula (D)
• d. deprotecting the compound of formula (D), to obtain a compound of formula (E) and
• e. hydrolyzing the compound of formula (E) to provide the compound of formula (I).