Sodium Bicarbonate → Di-tert-butyl (chloromethyl) phosphate

HRID 1367680

반응식

HRID 1367680 반응식
[P:1]([O-:13])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[K+].C(=O)(O)[O-].[Na+].[Cl:20][CH2:21]OS(Cl)(=O)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.ClCCl>[Cl:20][CH2:21][O:2][P:1](=[O:13])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10]

참가 물질

7

반응물 3

HCID 516892Sodium BicarbonateHCID 2733556Chloromethyl chlorosulfateHCID 23674467Potassium di-tert-butyl phosphate

생성물 1

HCID 11701630Di-tert-butyl (chloromethyl) phosphate

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

According to a literature procedure (Tetrahedron Letters; 2002, 43, 3793), compound I was prepared as follows: Potassium di-tert-butyl phosphate (6.35 g), tetra-n-butylammonium hydrogen sulphate (917 mg) and sodium bicarbonate (8.96 g) were dissolved in water (230 mL). Dichloromethane was added (130 mL) and the resulting mixture was cooled down to 0° C. A solution of chloromethylchlorosulphate (917 mg) in dichloromethane (100 mL) was slowly added under vigorous stirring. The reaction mixture was allowed to reach room temperature and further stirred overnight at this temperature. The organic layer was then separated, washed with brine (50 mL), dried over Na2SO4 and concentrated under vacuum. The desired product 1 was obtained as a colourless oil (2.4 g). Phosphoric acid di-tert-butyl ester chloromethyl ester 1. Colourless oil, 1H-NMR (CDCl3) δ 5.65 (d, J=15.0 Hz, 2H), 1.52 (s, 18H); 13C-NMR (CDCl3) δ 84.2 (d, J=7.6 Hz), 73.3 (d, J=6.9 Hz), 29.8 (d, J=4.3 Hz); 31P-NMR (CDCl3) δ −11.8.

후처리

  1. customwas prepared
  2. customThe organic layer was then separated
  3. washwashed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-36e62a7cf9894c37bd01ef5ae2e856ac
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893271B2

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