Diketene → HCID 11513976, 화합물

HRID 1184024노트

반응식

HRID 1184024 반응식
[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]

참가 물질

5

반응물 2

HCID 12661DiketeneHCID 6375161-Phenylethanol, (R)-

생성물 1

HCID 11513976HCID 11513976, 화합물수율 100%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fae3b861a92f40fe8e5bc03001f00913
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664399B2

반응 노트

불러오는 중…