Benzyl Bromide → HCID 68676580, compound

HRID 639936Notes

Reaction equation

HRID 639936 reaction equation
[H-].[Na+].[CH2:3](Br)C1C=CC=CC=1.CON(C)[C:14](=[O:38])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C[Li]>>[CH2:31]([O:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14](=[O:38])[CH3:3])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86039215HCID 86039215, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 68676580HCID 68676580, compound

Procedure

More specifically, compound (I) where R1, R3, R4, R5 are methyl groups, R2 is a hydroxyl group, m=1 and n=13 can be prepared in the following manner: Oxacycloheptadecan-2-one reacts with dimethylhydroxylamine in the presence of trimethylaluminium at 0° C. and at atmospheric pressure to yield N-methoxy-N-methyl-16-hydroxyhexadecanamide. The hydroxy function of this compound is then protected in the presence of sodium hydride and benzyl bromide at −78° C. and atmospheric pressure. The resulting N-methoxy-N-methyl-16-benzyloxyhexadecanamide is subsequently treated with methyllithium at −78° C. and at atmospheric pressure to yield 17-benzyloxyheptadecan-2-one. This reacts with the vinylmagnesium to afford 18-benzyloxy-3-methyloctadec-1-en-3-ol that in the presence of trimethylhydroquinone, zinc chloride and concentrated hydrochloric acid yields 2-(15-benzyloxypentadecyl)-2,5,7,8-tetramethylchroman-6-ol. Catalytic hydrogenation of this compound in the presence of palladium on charcoal affords 2-(15-hydroxypentadecyl)-2,5,7,8-tetramethylchroman-6-ol.

Sources & evidence

ORD record
ord-c549b160b39546e6a3afa90fca2ee2b3
Source dataset
uspto-grants-2010_04
Patent number
US07691900B2

Reaction notes

Loading…