Benzaldehyde → HCID 11637126, compound

HRID 1069205Notes

Reaction equation

HRID 1069205 reaction equation
C([Li])CCC.[CH3:6][C:7]1[S:8][CH:9]=[CH:10][C:11]=1[CH3:12].[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+]>C1COCC1>[CH3:12][C:11]1[CH:10]=[C:9]([CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[OH:20])[S:8][C:7]=1[CH3:6]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 25517Ammonium ChlorideHCID 342952,3-DimethylthiopheneHCID 178418339Butyllithium

Product 1

HCID 11637126HCID 11637126, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

n-Butyl lithium (19.6 ml, 49.1 mmol, 2.5 N in hexanes) was added dropwise to a stirred solution of 2,3-dimethyl-thiophene (5.0 g, 44.6 mmol) in THF (100 mL) at −78° C. under a dry nitrogen atmosphere. The solution was warmed to 0° C. for 30 min and recooled to −78° C. whereupon benzaldehyde (5.0 mL, 49.1 mmol ) was added. After an additional 45 minutes, sat. aq. ammonium chloride was added and the reaction mixture was partitioned between water and ether. The ether phase was washed with brine and concentrated. The resultant oil was triturated with pet. ether to provide the title compound as a white solid (7.77 g, 80%): mp 80-81° C.: NMR (CDCl3); δ7.45 (ddd, J=8, 1, 1 Hz, 2H), 7.37 (ddd, J=8, 8, 1 Hz, 2H), 7.3 (m, 1H), 6.57 (s, 1H), 6.93 (s, 1H, OH), 2.29 (s, 3H), 2.05 (s, 3H); MS (EI) (M+) 218 (45%, MI): Anal. Calc. for C13H14OS: C, 71.52; H, 6.46; N, 0.00. Found: C, 71.41; H, 6.42; N, 0.09.

Workup

  1. additionwas added
  2. customthe reaction mixture was partitioned between water and ether
  3. washThe ether phase was washed with brine
  4. concentrationconcentrated
  5. customThe resultant oil was triturated with pet. ether

Sources & evidence

ORD record
ord-e268daf6277a433eaa5545f6f72e4a0e
Source dataset
uspto-grants-2001_06
Patent number
US06251936B1

Reaction notes

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