Sodium borohydride → {4-[8-Hydroxymethyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl]-phenyl}-acetic acid methyl ester

HRID 898676Notes

Reaction equation

HRID 898676 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]3[C:20](=[C:21]([CH:23]=[O:24])[CH:22]=2)[O:19][C:18]([CH3:26])([CH3:25])[CH2:17][C:16]3([CH3:28])[CH3:27])=[CH:7][CH:6]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]3[C:20](=[C:21]([CH2:23][OH:24])[CH:22]=2)[O:19][C:18]([CH3:25])([CH3:26])[CH2:17][C:16]3([CH3:28])[CH3:27])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59692068HCID 59692068, compound2×

Product 1

HCID 59692069{4-[8-Hydroxymethyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl]-phenyl}-acetic acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred, cooled (ice bath) solution of {4-[8-formyl-2,2,4,4-tetramethyl chroman-6-ylethynyl]-phenyl}-acetic acid methyl ester (Compound 45, 0.21 g, 0.58 mmol) in methanol (4 mL) was treated with sodium borohydride (0.024 g, 0.64 mmol) and the resulting reaction mixture was stirred for 2 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 afford the title product as a colorless oil (0.21 g, 100%).

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

Sources & evidence

ORD record
ord-1707f1a75690442a9213101b7eb14f6d
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

Loading…