Diketene → HCID 11513976、化合物

HRID 1184024ノート

反応式

HRID 1184024 の反応式
[C:1]1([C@H:7]([OH:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]=[C:11]1[O:14][C:13](=[O:15])[CH2:12]1>O1CCCC1.CN(C1C=CN=CC=1)C>[O:14]=[C:11]([CH3:10])[CH2:12][C:13]([O:9][C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])=[O:15]

参加物

5

反応物 2

HCID 12661DiketeneHCID 6375161-Phenylethanol, (R)-

生成物 1

HCID 11513976HCID 11513976、化合物収率 100%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (R)-1-phenylethanol (6.0 ml, 50 mmol) in dry tetrahydrofuran (75 ml) at room temperature was added 4-(N,N-dimethylamino)pyridine (610 mg, 5.0 mmol) followed by dropwise addition of 4-methyleneoxetan-2-one (3.83 ml, 50 mmol). The reaction was stirred for 12 hours at room temperature, then the solvent removed under reduced pressure. The residue was dissolved in ethyl acetate, poured into a separatory funnel, and washed with 1M aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate, then brine. The organic phase was separated and the solvent removed under resuced pressure to provide (R)-1-phenylethyl 3-oxobutanoate as a light reddish oil (10.3 g, 100%). 1H NMR (CDCl3, 400 MHz) δ 7.4-7.2 (m, 5H); 5.94 (q, 1H, J=6.6 Hz); 3.45 (s, 2H); 2.22 (s, 3H); 1.56 (d, 3H, J=6.6 Hz).

後処理

  1. customthe solvent removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. additionpoured into a separatory funnel
  4. washwashed with 1M aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate
  5. customThe organic phase was separated
  6. customthe solvent removed under resuced pressure

出典と根拠

ORDレコード
ord-fae3b861a92f40fe8e5bc03001f00913
出典データセット
uspto-grants-2014_03
特許番号
US08664399B2

反応ノート

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