Sodium borohydride → HCID 15307873, compound

HRID 898349Notes

Reaction equation

HRID 898349 reaction equation
[BH4-].[Na+].[CH2:3]([C:5]1[O:6][C:7]2[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=2[C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11])[CH3:4]>C(O)C>[CH2:3]([C:5]1[O:6][C:7]2[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=2[C:9]=1[CH:10]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:11])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12391264(2-Ethyl-3-benzofuranyl)phenylmethanone

Product 1

HCID 15307873HCID 15307873, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (7.26 g; 0.192 mol) was added portionwise to the mixture of (2-ethyl-benzofuran-3-yl)-phenyl-methanone (24 g; 0.096 mol) in ethanol (300 mL) while stirring and cooling in ice bath under an atmosphere of nitrogen. The mixture was stirred at room temperature for one hour and the solvent was then evaporated. The residue was extracted with ether and the ethereal extracts were washed with water, dried over anhydrous magnesium sulfate and the solvent was evaporated to give a yellow solid (22.5 g), m.p. 98-99° C. Mass spectrum (ESI, [M+] m/z 252. 1HNMR (400 MHz, DMSO-d6): δ 1.24 (t, 3H, J=7.69 Hz), 2.91 (q, 2H, J=7.69 Hz), 5.86 (d, 1H, J=3.7 Hz), 5.98 (d, 1H, J=3.7 Hz), 7.06 (dt, 1H, J=7.25, 0.9 Hz), 7.13-7.21 (m, 2H), 7.28-7.32 (m, 2H), 7.4-7.46 (m, 4H). Elemental Analysis for C17H16O2: Calculated: C, 80.93; H, 6.39. Found: C, 81.03; H, 6.31.

Workup

  1. temperaturecooling in ice bath under an atmosphere of nitrogen
  2. stirringThe mixture was stirred at room temperature for one hour
  3. customthe solvent was then evaporated
  4. extractionThe residue was extracted with ether
  5. washthe ethereal extracts were washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f2c2555178784694af7b346417d6036e
Source dataset
uspto-grants-2008_04
Patent number
US07351726B2

Reaction notes

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