Triethylamine → Phosphoric acid 3-[3-(4-bromo-phenyl)-benzo [d]isothiazol-6-yl]-1,1-dimethyl-prop-2-ynyl ester diethyl ester

HRID 270457노트

반응식

HRID 270457 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]#[C:18][C:19]([CH3:22])([OH:21])[CH3:20])=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1.[Li+].CCC[CH2-].C(N(CC)CC)C.[CH2:35]([O:37][P:38](Cl)([O:40][CH2:41][CH3:42])=[O:39])[CH3:36]>C1COCC1.CCCCCC.O>[CH2:35]([O:37][P:38](=[O:39])([O:40][CH2:41][CH3:42])[O:21][C:19]([CH3:22])([CH3:20])[C:18]#[C:17][C:15]1[CH:14]=[CH:13][C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)=[N:9][S:10][C:11]=2[CH:16]=1)[CH3:36]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 61028n-Butyl lithiumHCID 223138854-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-2-methyl-but-3-yn-2-ol

생성물 1

HCID 69289237Phosphoric acid 3-[3-(4-bromo-phenyl)-benzo [d]isothiazol-6-yl]-1,1-dimethyl-prop-2-ynyl ester diethyl ester수율 33%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

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온도
0 °C

실험 절차

200 mg (0.54 mmol) 4-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-2-methyl-but-3-yn-2-ol in 2 ml THF were treated with 36 μl (5.6 mmol) 1.6 M N-Butyllithium in hexane at −78° C. for 30 min. 112 μl (0.81 mmol, 1.5 eq) Triethylamine in 0.5 ml THF and 117 μl (0.8 mmol, 1.5 eq) Diethylchlorophosphate in 0.5 ml THF were added and the solution was stirred at −78° C. over night and at 0° C. for 4 h. Water was added, and the inorganic phase was extracted with EtOAc, the combined organic phases were washed with brine and dried over Na2SO4. Column chromatography on silica gel with hexane:EtOAc 3:1 gave 90 mg (33%) Phosphoric acid 3-[3-(4-bromo-phenyl)-benzo[d]isothiazol-6-yl]-1,1-dimethyl-prop-2-ynyl ester diethyl ester as yellow semisolid, MS: 508 (MH+, 1Br).

후처리

  1. extractionthe inorganic phase was extracted with EtOAc
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4

출처 및 근거

ORD 기록
ord-e83b355ebd0d4ccc94882547bd1e0227
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449483B2

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