Methanol → (R)-1-(3-nitrophenyl)ethanol

HRID 2300888ノート

反応式

HRID 2300888 の反応式
CB1N2CCC[C@H]2C(C2C=CC=CC=2)(C2C=CC=CC=2)O1.B.[CH3:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=1)=[O:25].CO>C(Cl)Cl>[N+:32]([C:28]1[CH:27]=[C:26]([C@H:24]([OH:25])[CH3:23])[CH:31]=[CH:30][CH:29]=1)([O-:34])=[O:33]

参加物

5

反応物 3

HCID 887MethanolHCID 8494m-NitroacetophenoneHCID 178419160HCID 178419160、化合物

生成物 1

HCID 11147933(R)-1-(3-nitrophenyl)ethanol収率 96.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (S)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]- [1,3,2]-oxazaborole-borane (6.06 mmol) in CH2Cl2 (6 mL) at −20° C. was added a solution of 3-nitroacetophenone (6.06 mmol) in CH2Cl2 (6 mL) in a dropwise fashion over 30 min. The resulting mixture was stirred 45 min. longer then poured into cold methanol (−20° C.), and this mixture allowed to stir overnight while warming to room temperature. The mixture was then concentrated in vacuo then more methanol (100 mL) added and concentrated, and then added another 100 mL methanol and concentrated. The resulting crude was purified on silica gel in 60:40 hexanes:ethyl acetate to yield 0.98 g of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.22 (m, 1H); 8.08 (m, 1H); 7.69 (d, J=7.8 Hz, 1H); 7.50 (t, J=7.8 Hz, 1H); 5.00 (m, 1H); 2.62 (s, 1H); 1.53 (d, J=7.1 Hz, 3H).

後処理

  1. stirringto stir overnight
  2. concentrationThe mixture was then concentrated in vacuo
  3. additionmore methanol (100 mL) added
  4. concentrationconcentrated
  5. additionadded another 100 mL methanol
  6. concentrationconcentrated
  7. customThe resulting crude was purified on silica gel in 60:40 hexanes

出典と根拠

ORDレコード
ord-17012c13bdda464bba5b0f8e71c0433a
出典データセット
uspto-grants-2002_12
特許番号
US06498165B1

反応ノート

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