Hydrochloric Acid → HCID 54113268, compound

HRID 1579618Notes

Reaction equation

HRID 1579618 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][C:15]([C:17]([CH2:19][Cl:20])=[O:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4].O.Cl>CO>[Cl:20][CH2:19][CH:17]([OH:18])[C:15]1[O:16][C:12]([C:9]2[CH:10]=[CH:11][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 213893612-Chloro-1-[5-(4-nitrophenyl)furan-2-yl]ethan-1-one

Product 1

HCID 54113268HCID 54113268, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (1.6 g, 0.043 mole) was added in portions to a stirred mixture of 11.5 g (0.043 mole) of chloromethyl 5-(p-nitrophenyl)-2-furyl ketone in 150 ml of absolute methanol over 10 minutes at 15°-20°. The resulting solution was stirred at ambient temperature for 2.5 hours, poured into a mixture of ice and water (400 ml), and made acidic with 5% aqueous HCl. The yellow solid was collected by filtration and washed with water to give 11.5 g (100%) of title compound. Recrystallization from a MeOH--H2O mixture gave an analytical sample, m.p. 111°-113°.

Workup

  1. filtrationThe yellow solid was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-31b03cfc76ea4a09975c11203fe9c16d
Source dataset
uspto-grants-1976_01
Patent number
US03931247

Reaction notes

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