Dichloromethane → HCID 18182320, compound

HRID 1359413Notes

Reaction equation

HRID 1359413 reaction equation
O[CH:2]([C:9]1[C:10]2[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][C:11]=2[S:12][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([BH3-])#N.[Na+].ClCCl>[I-].[Zn+2].[I-].CO>[CH2:2]([C:9]1[C:10]2[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][C:11]=2[S:12][CH:13]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 18182224HCID 18182224, compound

Product 1

HCID 18182320HCID 18182320, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 8.3 g of 3-(α-hydroxybenzyl)-6-ethoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]thiophene, 12.5 g of zinc iodide, 2.0 g of sodium cyanoborohydride and 150 ml of dichloromethane was stirred at room temperature for 3 hours. After adding methanol to the reaction solution, insoluble matters were filtered off. The solvent was removed, and the residue was subjected to silica gel column chromatography and eluted with hexane and then with hexane/ethyl acetate (10:1), to give 5.9 g of the target compound.

Workup

  1. filtrationwere filtered off
  2. customThe solvent was removed
  3. washeluted with hexane

Sources & evidence

ORD record
ord-d1090ac100cc49bfb0d0601bb096aff4
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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