1-Indanone, 6-bromo- → 6-bromo-2,3-dihydro-1H-inden-1-ol

HRID 896068ノート

反応式

HRID 896068 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:11])=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 1397781-Indanone, 6-bromo-HCID 4311764Sodium borohydride

生成物 1

HCID 27548246-bromo-2,3-dihydro-1H-inden-1-ol収率 100%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 6-bromo-1-indanone (prepared as described by Cornelius, Lyndon A. M. and Combs, Donald W. Synth. Commun. (1994), 24(19), 2777-88) (1.4 g, 6.57 mmol) in 20 mL of methanol was added sodium borohydride (0.087 g, 2.3 mmol) over a period of five minutes at room temperature. The reaction mixture was stirred for two hours at room temperature, concentrated under pressure and partitioned between ethyl acetate (50 mL) and 1N HCl (20 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure to yield the title compound as a solid (1.4 g, 99%). 1H NMR (CDCl3): δ 7.45 (s, 1H), 7.3 (d, 1H), 7.0 (d, 1H), 5.2 (t, 1H), 2.9 (m, 1H), 2.7 (m, 1H), 2.4 (m, 1H), 1.9 (m, 2H).

後処理

  1. concentrationconcentrated under pressure
  2. custompartitioned between ethyl acetate (50 mL) and 1N HCl (20 mL)
  3. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-e2d1d48b2e634a9784938743713600a1
出典データセット
uspto-grants-2005_07
特許番号
US06919335B2

反応ノート

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