Diisobutylaluminumhydride → HCID 67235638, compound

HRID 69092Notes

Reaction equation

HRID 69092 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([CH2:12][Br:13])=[CH:8][C:9]=1[O:10][CH3:11])=O.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[Br:13][CH2:12][C:7]1[S:6][C:5]([CH2:3][OH:2])=[C:9]([O:10][CH3:11])[CH:8]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 67235324HCID 67235324, compound

Product 1

HCID 67235638HCID 67235638, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromomethyl-3-methoxy-thiophene-2-carboxylic acid methyl ester (1.4 g, 5.2 mmol) in anhydrous dichloromethane (50 mL) is added diisobutyl aluminum hydride (1M in hexane, 21.0 mL, 21.1 mmol) dropwise at −78° C. After the completion of the addition, the mixture is warmed to room temperature and stirred for 2 hours. The reaction mixture is quenched with water (15 mL) at −40° C. and the mixture is agitated for 30 minutes at room temperature. The reaction mixture is filtered through diatomaceous earth. The filtrate is dried over sodium sulfate and concentrated, to give the title compound as a pale yellow liquid (1.2 g, 96%). 1H NMR (400 MHz, d6 DMSO) 7.46 (s, 1H), 4.58 (s, 2H), 3.84 (s, 3H), 3.73 (s, 2H).

Workup

  1. additionAfter the completion of the addition
  2. customThe reaction mixture is quenched with water (15 mL) at −40° C.
  3. stirringthe mixture is agitated for 30 minutes at room temperature
  4. filtrationThe reaction mixture is filtered through diatomaceous earth
  5. dry with materialThe filtrate is dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d6f55125d095497096119c4a82391f8b
Source dataset
uspto-grants-2014_09
Patent number
US08822486B2

Reaction notes

Loading…