Hydrochloric Acid → 1-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-carboxypyrrole

HRID 613631노트

반응식

HRID 613631 반응식
[Si:1]([O:18][CH2:19][C:20]1[C:21]([Cl:34])=[C:22]([N:27]2[CH:31]=[CH:30][CH:29]=[C:28]2[CH:32]=[O:33])[CH:23]=[CH:24][C:25]=1[Cl:26])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(=CC)C.P([O-])(O)(O)=[O:41].[Na+].Cl([O-])=O.[Na+].Cl>O.C(O)(C)(C)C>[Si:1]([O:18][CH2:19][C:20]1[C:21]([Cl:34])=[C:22]([N:27]2[CH:31]=[CH:30][CH:29]=[C:28]2[C:32]([OH:41])=[O:33])[CH:23]=[CH:24][C:25]=1[Cl:26])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 183218991-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-formylpyrroleHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

생성물 1

HCID 183217851-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-carboxypyrrole수율 71.9%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6386tert-Butanol용매

실험 절차

1-(3-tert-Butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-formylpyrrole (1.51 g) was dissolved in a mixture of water (8 ml) and tert-butyl alcohol (30 ml), and 2-methyl-2-butene (923 mg) and sodium dihydrogen phosphate (392 mg) were added to the mixture in water bath. To the mixture was added portionwise sodium chlorite (1.19 g), and the mixture was stirred for 1 day at the same temperature. The reaction mixture was cooled in an ice bath, adjusted to pH 4 with 1M hydrochloric acid and extracted with chloroform. The organic layer was separated, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with chloroform-n-hexane-methanol to give 1-(3-tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-carboxypyrrole (1.12 g) as an oil.

후처리

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. extractionextracted with chloroform
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with chloroform-n-hexane-methanol

출처 및 근거

ORD 기록
ord-dc72025d865c42409cded04b90c1064e
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008229

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