2-Cyclohexen-1-one → (Naphthalene-1-sulfonyl)-(3-oxo-cyclohexyl)-acetic acid methyl ester

HRID 602752노트

반응식

HRID 602752 반응식
[CH3:1][O:2][C:3](=[O:18])[CH2:4][S:5]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6].C[O-].[Na+].[C:22]1(=[O:28])[CH2:27][CH2:26][CH2:25][CH:24]=[CH:23]1>CO.[NH4+].[Cl-]>[CH3:1][O:2][C:3](=[O:18])[CH:4]([S:5]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)(=[O:6])=[O:7])[CH:24]1[CH2:25][CH2:26][CH2:27][C:22](=[O:28])[CH2:23]1

참가 물질

6

반응물 3

HCID 135942-Cyclohexen-1-oneHCID 10942334Sodium MethoxideHCID 67267336(Naphthalene-1-sulfonyl)-acetic acid methyl ester

생성물 1

HCID 67266832(Naphthalene-1-sulfonyl)-(3-oxo-cyclohexyl)-acetic acid methyl ester수율 49.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 25517Ammonium Chloride용매

실험 절차

To a stirred solution of 2.75 g (0.010 mol) of (naphthalene-1-sulfonyl)-acetic acid methyl ester in 100 mL of MeOH at RT, 0.19 mL (0.011 mol, 1.1 eq) of a solution of sodium methoxide (5.4 M in MeOH) were added. After 15 min, 1.1 g (0.011 mol, 1.1 eq) of 2-cyclohexen-1-one were added. The reaction mixture was stirred at RT for 3 hours followed by an additional 4 hours at 60° C., diluted with aqueous NH4Cl and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel with heptane/EtOAc (from 4:1 to 1:2) yielded 1.78 g (48%) of (naphthalene-1-sulfonyl)-(3-oxo-cyclohexyl)-acetic acid methyl ester as a racemic mixture of diastereomers, light orange oil, MS: 361 (MH+).

후처리

  1. waitfollowed by an additional 4 hours at 60° C.
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-b1df49c556cc415a8378d4c9a8c3b826
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906546B2

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