Triphenylphosphine → 2-oxo-2H-1-benzopyran-7-yl 4-methoxycarbonyloxybenzoate

HRID 2120514노트

반응식

HRID 2120514 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:20][C:21]1[CH:30]=[C:29]2[C:24]([CH:25]=[CH:26][C:27](=[O:31])[O:28]2)=[CH:23][CH:22]=1.[CH3:32][O:33][C:34]([O:36][C:37]1[CH:45]=[CH:44][C:40]([C:41](O)=[O:42])=[CH:39][CH:38]=1)=[O:35].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:32][O:33][C:34]([O:36][C:37]1[CH:45]=[CH:44][C:40]([C:41]([O:20][C:21]2[CH:22]=[CH:23][C:24]3[CH:25]=[CH:26][C:27](=[O:31])[O:28][C:29]=3[CH:30]=2)=[O:42])=[CH:39][CH:38]=1)=[O:35]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5281426UmbelliferoneHCID 222422684-[(Methoxycarbonyl)oxy]benzoic acid

생성물 1

HCID 234351152-oxo-2H-1-benzopyran-7-yl 4-methoxycarbonyloxybenzoate수율 70.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

13.4 g triphenylphosphine is added to a solution of 8.3 g 7-hydroxycoumarin, 10.0 g 4-methoxycarbonyloxybenzoic acid, 8.9 g diethyl azodicarboxylate and 50 ml tetrahydrofuran at 0° C. The reaction mixture was stirred overnight at room temperature, filtered to remove inorganic material and the filtrate evaporated down, taken up in warm hexane, filtered to remove inorganic material and evaporated down again. The residue is purified by column chromatography on silica gel using hexane/ethyl acetate (1/1 v/v) as eluent and recrystallisation from acetonitrile to yield 12.2 g of 2-oxo-2H-1-benzopyran-7-yl 4-methoxycarbonyloxybenzoate.

후처리

  1. filtrationfiltered
  2. customto remove inorganic material
  3. customthe filtrate evaporated down
  4. filtrationfiltered
  5. customto remove inorganic material
  6. customevaporated down again
  7. customThe residue is purified by column chromatography on silica gel
  8. customrecrystallisation from acetonitrile

출처 및 근거

ORD 기록
ord-12c2b528fafa40829cf1317985f30be4
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06692797B1

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