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Triethylamine → Tert-butyl 4-(2-formyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 252402
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인쇄 미리보기

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HRID 252402 반응식
C(N(CC)CC)C.[OH:8][CH2:9][CH:10]([CH:26]([CH3:28])[CH3:27])[CH2:11][CH:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].S(=O)(=O)(O)[O-].[K+]>CS(C)=O.ClCCl>[CH:9]([CH:10]([CH:26]([CH3:28])[CH3:27])[CH2:11][CH:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:8]
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 516920Potassium bisulfateHCID 66888909Tert-butyl 4-(2-hydroxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

생성물 1

HCID 86618882Tert-butyl 4-(2-formyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매
HCID 6344
Dichloromethane
용매

반응 조건

온도
0 °C

실험 절차

6.97 ml of triethylamine are added dropwise at 0° C. to the solution of 3.0 g of tert-butyl 4-(2-hydroxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate in 11 ml of dimethyl sulphoxide and 55 ml of dichloromethane. 5.23 g of sulphur trioxide-pyridine complex are added in 3 portions at intervals of 10 minutes and the reaction mixture is stirred at 0° C. for a further 3 hours. The reaction mixture is poured onto ice-water, adjusted to pH=2.5 with saturated aqueous potassium bisulphate solution and extracted with diethyl ether (3×)—the combined organic phases are washed successively with water and 5% aqueous sodium hydrogencarbonate solution, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue as a yellow oil. Rf=0.46 (1:2 EtOAc-heptane).

후처리

  1. addition5.23 g of sulphur trioxide-pyridine complex are added in 3 portions at intervals of 10 minutes
  2. additionThe reaction mixture is poured onto ice-water
  3. extractionextracted with diethyl ether (3×)—the combined organic phases
  4. washare washed successively with water and 5% aqueous sodium hydrogencarbonate solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-a81b7783e60f47d798116e7d9858815f
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07868036B2

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