Water → HCID 14685353, compound

HRID 892977Notes

Reaction equation

HRID 892977 reaction equation
C([Li])CCC.[CH3:6][O:7][CH2:8][C:9]1[CH:13]=[CH:12][S:11][CH:10]=1.CN(C)[CH:16]=[O:17].O>CCOCC>[CH3:6][O:7][CH2:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[CH:16]=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 12197664HCID 12197664, compoundHCID 178418339Butyllithium

Product 1

HCID 14685353HCID 14685353, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Reaction of 3-bromomethylthiophene with sodium methoxide in methanol provided 3-methoxymethylthiophene (84%). n-Butyl lithium (30 ml, 1.5 M, 45 mmol) was slowly added to 3-methoxymethylthiophene (5.0 g, 39 mmol) in dry ether (100 ml) at 25° C. After stirring for 1 h, N,N-dimethylformamide (5.7 g, 78 mmol) in dry ether (200 ml) was added dropwise and the resultant solution was stirred for an additional 18 h at 20° C. Water (5 ml) was added and the organic phase washed with 5% hydrochloric acid (100 ml) followed by water (100 ml) and dried. The solvent was removed to yield the crude product (5.2 g, 85%) which was essentially pure by n.m.r. Distillation afforded the title compound (3.80 g, 62%) as a colourless oil, b.p. 73°-75° C. at 0.25 mmHg (Found M+ : 156.0256. C7H8O2S requires M, 156.0245) which showed νmax (film) 667m, 1107m, 1200w, 1426m, 1662s, 2930w and 3100w cm-1 ; δH (CCl4) 3.35 (3H, s), 4.66 (2H, s), 7.05 (1H, d, J 5 Hz), 7.49 (1H, d, J 5 Hz), 9.87 (1H, s); m/z 156 (M+), 141 (M+ -CH3).

Workup

  1. washthe organic phase washed with 5% hydrochloric acid (100 ml)
  2. customdried
  3. customThe solvent was removed
  4. customto yield the crude product (5.2 g, 85%) which
  5. distillationDistillation

Sources & evidence

ORD record
ord-fcdffc3fae3a4863817c9a83d2edb98d
Source dataset
uspto-grants-1992_06
Patent number
US05120861

Reaction notes

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