tert-Butanol → methyl 2-methyl-6-[(1R,3S)-3-(2-oxoethoxy)cyclohexyloxymethyl]benzoate

HRID 1353166노트

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HRID 1353166 반응식
[CH2:1]([O:4][C@H:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([O:11][CH2:12][C:13]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:14]=2[C:15]([O:17][CH3:18])=[O:16])[CH2:6]1)[CH:2]=C.I([O-])(=O)(=O)=[O:25].[Na+].C(O)(C)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)C.O.[Os](=O)(=O)(=O)=O>[CH3:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:13]([CH2:12][O:11][C@@H:7]2[CH2:8][CH2:9][CH2:10][C@H:5]([O:4][CH2:1][CH:2]=[O:25])[CH2:6]2)[C:14]=1[C:15]([O:17][CH3:18])=[O:16]

참가 물질

8

반응물 4

HCID 6386tert-ButanolHCID 24477Sodium ThiosulfateHCID 23667635Sodium periodateHCID 58864607HCID 58864607, 화합물

생성물 1

HCID 58864603methyl 2-methyl-6-[(1R,3S)-3-(2-oxoethoxy)cyclohexyloxymethyl]benzoate

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 962Water용매HCID 3283Diethyl Ether용매

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온도
0 °C

실험 절차

1.0 g of methyl 2-((1R,3S)-3-allyloxycyclohexyloxymethyl)-6-methylbenzoate is dissolved in 30 ml of diethyl ether, and 2.0 g of sodium periodate, dissolved in 30 ml of water, are added. At 0° C., 2 ml of a solution of 2.5% by weight of osmium tetroxide and tert-butanol are added. The reaction mixture is stirred vigorously for three hours. The mixture is then cooled to 0° C., and 50 ml of a saturated sodium thiosulfate solution are added. The organic phase is removed. The aqueous phase is extracted three times with in each case 20 ml of diethyl ether. The combined organic phases are dried over magnesium sulfate and the solvent is then removed under reduced pressure. This gives 1.0 g of methyl 2-methyl-6-[(1R,3S)-3-(2-oxoethoxy)cyclohexyloxymethyl]benzoate as a yellow oil C18H24O5 (320.39), MS(ESI): 321 (M+H+), Rf=0 23 (n-heptane:ethyl acetate=1:1).

후처리

  1. additionare added
  2. customThe organic phase is removed
  3. extractionThe aqueous phase is extracted three times with in each case 20 ml of diethyl ether
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. customthe solvent is then removed under reduced pressure

출처 및 근거

ORD 기록
ord-6b8544f26c8940a39d3e21cdba91d550
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220876B2

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