Water → HCID 14326169, compound

HRID 372910Notes

Reaction equation

HRID 372910 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:11][C:12]1[CH:16]=[CH:15][S:14][CH:13]=1.O>CN(C=O)C>[O:7]([CH2:11][C:12]1[CH:16]=[CH:15][S:14][CH:13]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24758Sodium hydrideHCID 124874623-(Chloromethyl)thiophene

Product 1

HCID 14326169HCID 14326169, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of phenol (13.16 g) in DMF (10 ml) was added in portions over 10 minutes to a stirred suspension of sodium hydride (3.12 g) in DMF (100 ml). After 2 hours, a solution of 3-(chloromethyl)thiophene (14.50 g) in DMF (30 ml) was added in one portion and the resulting mixture was stirred at room temperature for 3 hours then poured into water and extracted with ether. The extracts were washed successively with water, dilute aqueous sodium hydroxide, and aqueous sodium chloride, then dried and concentrated to give 3-(phenoxymethyl)thiophene (18.86 g, 91% yield) as a white solid. An analytical sample, recrystallised from methanol, had mp 49°-50°C.

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed successively with water, dilute aqueous sodium hydroxide, and aqueous sodium chloride
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-afbfab75b38346deb2e2399c2af1b89c
Source dataset
uspto-grants-1992_11
Patent number
US05160364

Reaction notes

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