Aluminium lithium hydride → 6-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-[2-hydroxyethoxy]phenyl]benzo[b]thiophene

HRID 1595042Notes

Reaction equation

HRID 1595042 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:13]([O:23][CH3:24])[CH:12]=3)=[C:8]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33](OC)=[O:34])=[CH:27][CH:26]=3)[S:7][C:6]=2[CH:37]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:13]([O:23][CH3:24])[CH:12]=3)=[C:8]([C:25]3[CH:26]=[CH:27][C:28]([O:31][CH2:32][CH2:33][OH:34])=[CH:29][CH:30]=3)[S:7][C:6]=2[CH:37]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 217063346-Hydroxy-2-[4-(2-methoxy-2-oxoethoxy)phenyl]-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophene

Product 1

HCID 217063306-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-[2-hydroxyethoxy]phenyl]benzo[b]thiopheneYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-hydroxy-2-[4-(2-methoxy-2-oxoethoxy)phenyl]-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophene (36 mg) in THF (2 mL) was added lithium aluminum hydride (16 mg) and the mixture was stirred under argon at ambient temperature for 1 h. The reaction was quenched with water (1 mL) and sodium hydroxide solution (1.0 M, 1 mL) while stirring continued for 30 min. The mixture was then diluted with brine (50 mL) and extracted with dichloromethane (30 mL×3). The combined organic layers were dried with sodium sulfate and concentrated in vacuo. Chromatography with Et3N:MeOH:EtOAc (5:10:85) afforded the product (29 mg).

Workup

  1. customThe reaction was quenched with water (1 mL) and sodium hydroxide solution (1.0 M, 1 mL)
  2. stirringwhile stirring
  3. waitcontinued for 30 min
  4. additionThe mixture was then diluted with brine (50 mL)
  5. extractionextracted with dichloromethane (30 mL×3)
  6. dry with materialThe combined organic layers were dried with sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6511e96f90124dc2871007e03a5f8c89
Source dataset
uspto-grants-2001_09
Patent number
US06284756B1

Reaction notes

Loading…