Lithium borohydride → (E)-7-[3-(3,4-bis-Hydroxymethylbenzyloxy)phenyl]-3-ethyloct-6-en-3-ol

HRID 2120477Notes

Reaction equation

HRID 2120477 reaction equation
[CH2:1]([C:3]([OH:33])([CH2:31][CH3:32])[CH2:4][CH2:5]/[CH:6]=[C:7](/[C:9]1[CH:10]=[C:11]([CH:28]=[CH:29][CH:30]=1)[O:12][CH2:13][C:14]1[CH:15]=[C:16]([C:24](OC)=[O:25])[C:17](=[CH:22][CH:23]=1)[C:18](OC)=[O:19])\[CH3:8])[CH3:2].[BH4-].[Li+]>>[OH:25][CH2:24][C:16]1[CH:15]=[C:14]([CH:23]=[CH:22][C:17]=1[CH2:18][OH:19])[CH2:13][O:12][C:11]1[CH:10]=[C:9](/[C:7](/[CH3:8])=[CH:6]/[CH2:5][CH2:4][C:3]([CH2:31][CH3:32])([OH:33])[CH2:1][CH3:2])[CH:30]=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 4148881Lithium borohydrideHCID 23439764dimethyl 4-[3-((E)-5-ethyl-5-hydroxy-1-methylhept-1-enyl)phenoxymethyl]phthalate

Product 1

HCID 67533486(E)-7-[3-(3,4-bis-Hydroxymethylbenzyloxy)phenyl]-3-ethyloct-6-en-3-ol

Procedure

In a manner similar to Example 53(e), by reacting 131 mg (0.29 mmol) of dimethyl 4-[3-((E)-5-ethyl-5-hydroxy-1-methylhept-1-enyl)phenoxymethyl]phthalate with 25 mg (1.15 mmol) of lithium borohydride, a colourless oil is obtained (m=89 mg; Y=78%).

Workup

  1. customa colourless oil is obtained (m=89 mg; Y=78%)

Sources & evidence

ORD record
ord-215de56286014425a6b4ad59faa62455
Source dataset
uspto-grants-2004_02
Patent number
US06689922B1

Reaction notes

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