Aluminium lithium hydride → 1-{4-[3-(3,4-Bis-hydroxymethylbenzyloxy)phenyl]-2-thiophenyl}-1-propanol

HRID 2307575Notes

Reaction equation

HRID 2307575 reaction equation
C1(C([O:9][CH2:10][C:11]2[CH:12]=[C:13]([CH:31]=[CH:32][C:33]=2[CH2:34][O:35]C(C2C=CC=CC=2)=O)[CH2:14][O:15][C:16]2[CH:17]=[C:18]([C:22]3[CH:23]=[C:24]([C:27](=[O:30])[CH2:28][CH3:29])[S:25][CH:26]=3)[CH:19]=[CH:20][CH:21]=2)=O)C=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:31]=[CH:32][C:33]=1[CH2:34][OH:35])[CH2:14][O:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:23]=[C:24]([CH:27]([OH:30])[CH2:28][CH3:29])[S:25][CH:26]=2)[CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 226068641-{4-[3-(3,4-Bis(1-phenylmethanoyloxymethyl)benzyloxy)phenyl]-2-thiophenyl}-1-propanone

Product 1

HCID 101780871-{4-[3-(3,4-Bis-hydroxymethylbenzyloxy)phenyl]-2-thiophenyl}-1-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.3 g (7.3 mmol) of 1-{4-[3-(3,4-bis(1-phenylmethanoyloxymethyl)benzyloxy)phenyl]-2-thiophenyl}-1-propanone are dissolved in 10 mL of THF and added dropwise to a suspension of 1.1 g (29 mmol) of lithium aluminium hydride, and the mixture is stirred for 2 hours. After treatment of the reaction medium with 1.1 mL of water, 1.1 mL of 15% sodium hydroxide and 3.3 mL of water, the medium is filtered. After purification by chromatography on silica gel (eluent: 3 heptane/7 ethyl acetate), the desired product is obtained in the form of a colourless oil (m=773 mg; Y=28%).

Workup

  1. filtrationAfter treatment of the reaction medium with 1.1 mL of water, 1.1 mL of 15% sodium hydroxide and 3.3 mL of water, the medium is filtered
  2. customAfter purification by chromatography on silica gel (eluent: 3 heptane/7 ethyl acetate)

Sources & evidence

ORD record
ord-27df2f4a4b6149e09242e407cd6a0f45
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

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