Sodium borohydride → [4-(5-tert-Butyl-3-hydroxymethyl-4-isopropoxy-2-methyl-phenylethynyl)-phenyl]-acetic acid methyl ester

HRID 1869997Notes

Reaction equation

HRID 1869997 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]([O:23][CH:24]([CH3:26])[CH3:25])=[C:15]([CH:27]=[O:28])[C:14]=2[CH3:29])=[CH:7][CH:6]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]([O:23][CH:24]([CH3:26])[CH3:25])=[C:15]([CH2:27][OH:28])[C:14]=2[CH3:29])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 60029385HCID 60029385, compound2×

Product 1

HCID 60029384[4-(5-tert-Butyl-3-hydroxymethyl-4-isopropoxy-2-methyl-phenylethynyl)-phenyl]-acetic acid methyl esterYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred, cooled (ice bath) solution of [4-(5-tert-butyl-3-formyl-4-isopropoxy-2-methyl-phenylethynyl)-phenyl]-acetic acid methyl ester (Intermediate 142, 0.172 g, 0.42 mmol) in methanol (4 mL) was treated with sodium borohydride (0.02 g, 0.51 mmol) and the resulting reaction mixture was stirred for 1.5 h. The reaction mixture was quenched with water and extracted with diethyl ether. The organic phase was washed with water (×1) and brine (×1), dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue that was subjected to flash column chromatography over silica gel (230-400 mesh) using 15-20% ethyl acetate in hexane as the eluent to afford the title product as a white solid (0.15 g, 88%).

Workup

  1. customthe resulting reaction mixture
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with diethyl ether
  4. washThe organic phase was washed with water (×1) and brine (×1)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to a residue that

Sources & evidence

ORD record
ord-306124ad785a45e7ad2c6a901e88a6d1
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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