Benzaldehyde → Benzo[b]thiophen-2-yl(phenyl)methanol

HRID 1873120ノート

反応式

HRID 1873120 の反応式
C([Li])CCC.[CH:6]1[CH:7]=[CH:8][C:9]2[S:14][CH:13]=[CH:12][C:10]=2[CH:11]=1.[CH:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[S:14]1[C:13]([CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[OH:22])=[CH:12][C:10]2[CH:11]=[CH:6][CH:7]=[CH:8][C:9]1=2

参加物

5

反応物 3

HCID 240BenzaldehydeHCID 7221Benzo(B)ThiopheneHCID 178418339Butyllithium

生成物 1

HCID 3311304Benzo[b]thiophen-2-yl(phenyl)methanol収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

n-Butyl lithium (35 ml, 2.5 N in hexanes) was added dropwise to a stirred solution of thianaphthene (11.5 g, 85.6 mmol) in THF (300 mL) at -78° C. under a dry N2 atmosphere. After 1 h, benzaldehyde (9.6 mL, 94.4 mmol) was added and the cold bath was removed. After an additional 30 minutes, sat. aq. NH4Cl was added and the reaction mixture was partitioned between water and ether. The ether phase was washed with brine and concentrated. The resultant solid was triturated with pet. ether and filtered to provide the title compound as a white solid (17.7 g, 86%): NMR (CDCl3); δ 7.78 (m, 1H, thiopheneH), 7.68 (m, 1H, thiopheneH), 7.22-7.56 (m, 7H), 7.12 (s, 1H, thiopheneH), 6.12 (d, 1H, OH), 2.51 (d, 1H, CH).

後処理

  1. customthe cold bath was removed
  2. waitAfter an additional 30 minutes
  3. additionsat. aq. NH4Cl was added
  4. customthe reaction mixture was partitioned between water and ether
  5. washThe ether phase was washed with brine
  6. concentrationconcentrated
  7. customThe resultant solid was triturated with pet. ether
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-45ae5792cb614e83987d570bd86d2517
出典データセット
uspto-grants-2000_08
特許番号
US06110962

反応ノート

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