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

HRID 1367680

反応式

HRID 1367680 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

HCID 11701630Di-tert-butyl (chloromethyl) phosphate

試薬・触媒・溶媒 3

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-36e62a7cf9894c37bd01ef5ae2e856ac
出典データセット
uspto-grants-2011_02
特許番号
US07893271B2

関連ノート

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