Menthol → Ethyl 2-phenylcyclopropane-1-carboxylate

HRID 487722

반응식

HRID 487722 반응식
C=CC1C=CC=CC=1.[N+](=CC(OCC)=O)=[N-].[C:17]1([C@@H:23]2[CH2:25][C@H:24]2[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(C)CCC(C(C)C)C(O)C1.C1([C@@H]2C[C@H]2C([O-])=O)C=CC=CC=1>ClCCl>[C:17]1([CH:23]2[CH2:25][CH:24]2[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

7

반응물 5

HCID 1254MentholHCID 7501StyreneHCID 12192Ethyl diazoacetateHCID 252496Ethyl trans-2-phenylcyclopropanecarboxylateHCID 6931403trans-2-Phenylcyclopropanecarboxylate

생성물 1

HCID 316914Ethyl 2-phenylcyclopropane-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a mixture of styrene (2.15g, 20.7 mmol) and Rh2 (4S-BNOX)4 (0.0113 g, 0.0131 mmol) in 5.0 mL of anhydrous dichloromethane was added, by syringe at room temperature, ethyl diazoacetate (0298 g, 2.62 mmol) in 3.0 mL of dichloromethane under nitrogen and at an addition rate of 0.8 mL/h (syringe pump). After addition was complete, the dichloromethane solution was passed through a plug of neutral alumina to separate the catalyst, and solvent and excess styrene were removed under reduced pressure Gas chromatographic separation of the trans-isomer produced a material whose specific rotation was -6.4° which corresponded to an enantiomeric excess of the ethyl (1R,2R)-2-phenylcyclopropanecarboxylate. Conversion of the ethyl esters to the 1-menthyl esters by base hydrolysis, acid chloride formation, and esterification with (-)-menthol provided a gas chromatographically separable mixture that showed 25% enantiomeric excess for the (1R,2R)-enantiomer of the trans-2-phenylcyclopropanecarboxylate.

후처리

  1. additionwas added, by syringe at room temperature
  2. additionAfter addition
  3. customto separate the catalyst, and solvent and excess styrene
  4. customwere removed under reduced pressure Gas chromatographic separation of the trans-isomer
  5. customproduced a material whose specific rotation
  6. customwas -6.4°
  7. customprovided a gas chromatographically separable mixture that

출처 및 근거

ORD 기록
ord-c342d840cbe84f84a8ffea54465dfe66
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05296595

연결된 노트

불러오는 중…