Triphenylphosphine → Methyl 4-(cis-2-phenyl-1-cyclohexanoyloxy)-2-methoxybenzoate

HRID 1677

반응식

HRID 1677 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:33]1([C@@H:39]2[CH2:44][CH2:43][CH2:42][CH2:41][C@H:40]2O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.N(C(OCC)=O)=N[C:48](OCC)=[O:49]>C1COCC1>[C:33]1([C@H:39]2[CH2:44][CH2:43][CH2:42][CH2:41][C@H:40]2[C:48]([O:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=2)=[O:49])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 102793rel-(1R,2S)-2-PhenylcyclohexanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12532676Methyl 4-hydroxy-2-methoxybenzoate

생성물 1

HCID 22883080Methyl 4-(cis-2-phenyl-1-cyclohexanoyloxy)-2-methoxybenzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (310 mg, 1.7 mmol) in dry THF (1.25 mL) was added triphenylphosphine (446 mg, 1.7 mmol) and the solution was cooled to 0° C. A 500 mL volume of trans-2-phenyl-1-cyclohexanol (200 mg, 1.35 mmol) and diethyl azodicarboxylate (319 μL, 2.02 mmol) in THF was added dropwise via addition funnel over 0.5 h. The reaction was filtered and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column packed in 92:8 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-(cis-2-phenyl-1-cyclohexanoyloxy)-2-methoxybenzoate.

후처리

  1. filtrationThe reaction was filtered
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was chromatographed on a silica gel column
  4. washEtOAc and eluted with same
  5. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-e05a7f6ef00b40218847ea8339f5616a
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726172

연결된 노트

불러오는 중…