Water → HCID 67092093, compound

HRID 2264558Notes

Reaction equation

HRID 2264558 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:16][C:14]=3[CH:15]=2)=[C:7]([C:27]#[N:28])[CH:6]=1)C.[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].O>C(O)C>[CH2:20]([C:17]1[CH:18]=[CH:19][C:13]2[O:12][C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][OH:3])=[CH:6][C:7]=3[C:27]#[N:28])=[CH:15][C:14]=2[CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 67091793HCID 67091793, compound

Product 1

HCID 67092093HCID 67092093, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Ethyl-4-(5-benzylbenzofuran-2-yl)-3-cyanobenzoate (0.05 g, 0.13 mmol), sodium borohydride (0.01 g, 0.26 mmol) and calcium chloride (0.015 g, 0.13 mmol) in ethanol (2.5 mL) were stirred at room temperature for 1 hour. Water was added and the aqueous layer was extracted with ethyl acetate (×2, 10 mL). Organic layer was washed with water and brine and dried over sodium sulphate in 75% yield: 1H NMR (400 MHz, CDCl3) δ 8.06 (d, 1H), 7.79 (s, 1H), 7.64 (d, 1H), 7.63 (s, 1H), 7.43-7.21 (m, 8H), 4.78 (s, 2H), 4.06 (s, 3H).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate (×2, 10 mL)
  2. washOrganic layer was washed with water and brine
  3. dry with materialdried over sodium sulphate in 75% yield

Sources & evidence

ORD record
ord-19bce8923beb4b79bbcf880c132206fb
Source dataset
uspto-grants-2010_12
Patent number
US07855193B2

Reaction notes

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