Sodium borohydride → HCID 11419613, compound

HRID 2106462Notes

Reaction equation

[CH3:1][C:2]([CH3:33])([CH3:32])[C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:18]=[CH:19][C:20]3[O:24][C:23]([C:25]([OH:27])=[O:26])=[C:22]([CH3:28])[C:21]=3[CH:29]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:30].[BH4-].[Na+]>>[CH2:13]([C:12]([C:17]1[CH:18]=[CH:19][C:20]2[O:24][C:23]([C:25]([OH:27])=[O:26])=[C:22]([CH3:28])[C:21]=2[CH:29]=1)([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:3]([OH:31])[C:2]([CH3:32])([CH3:33])[CH3:1])=[C:7]([CH3:30])[CH:8]=1)[CH2:15][CH3:16])[CH3:14]

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 11328417HCID 11328417, compound

Product 1

HCID 11419613HCID 11419613, compoundYield 71%

Procedure

5-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-3-methyl-benzofuran-2-carboxylic acid (170 mg g, 0.378 mmol) is reduced with NaBH4 (29 mg, 0.756 mmol) analogous to Example 3 to give the title product (120 mg, 71%).

Sources & evidence

ORD record: ord-a4de3f0803c04642b5e1ba97b6b445a3
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579488B2

Reaction notes

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