Ethyl cinnamyl carbonate → 1-Phenyl-1-phenoxy-2-propene

HRID 14441노트

반응식

HRID 14441 반응식
[O-:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].C(=O)(O[CH2:14][CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)OCC>>[C:17]1([CH:16]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:15]=[CH2:14])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

3

반응물 2

HCID 232463Ethyl cinnamyl carbonateHCID 4445035Phenolate Sodium

생성물 1

HCID 117359621-Phenyl-1-phenoxy-2-propene수율 81.3%

실험 절차

By the procedure for entry 9 of Table 1, the reaction of sodium phenoxide (232 mg, 2.00 mmol) and ethyl cinnamyl carbonate (192 mg, 0.930 mmol) with [(COD)IrCl]2 (6.7 mg, 0.010 mmol) and L1 (Sa,Sc,Sc) (10.8 mg, 0.0200 mmol) as catalyst was conducted at room temperature for 32 h. 1H NMR analysis of the crude reaction showed the ratios of branched to linear products to be 99/1. After purification, 159 mg of the title compound (75%) was isolated. HPLC analysis as described above indicated that the enantiomeric excess of the major product was 94%.

후처리

  1. custom1H NMR analysis of the crude reaction
  2. customAfter purification

출처 및 근거

ORD 기록
ord-cc18da941b554ad5b0897d3daa0d8ff2
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732365B2

반응 노트

불러오는 중…