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

HRID 1353166ノート

反応式

HRID 1353166 の反応式
[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]

参加物

8

反応物 4

HCID 6386tert-ButanolHCID 24477Sodium ThiosulfateHCID 23667635Sodium periodateHCID 58864607HCID 58864607、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6b8544f26c8940a39d3e21cdba91d550
出典データセット
uspto-grants-2007_05
特許番号
US07220876B2

反応ノート

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