N-Hydroxyphthalimide → Triphenylphosphine Oxide

HRID 1172154노트

반응식

HRID 1172154 반응식
CC[O:3]C(/N=N/C(OCC)=O)=O.C(OC(=O)CCCCCCCCCCCO)C1C=CC=CC=1.[C:35]1([P:41]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.ON1C(=O)C2=CC=CC=C2C1=O>C1COCC1.CCCCCC.C(OC(=O)C)C>[C:48]1([P:41](=[O:3])([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

참가 물질

7

반응물 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 12077613Dodecanoic acid, 12-hydroxy-, phenylmethyl ester

생성물 1

HCID 13097Triphenylphosphine Oxide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21226206Ethyl acetate hexane용매

실험 절차

Diethylazodicarboxylate (DEAD, 16.96 ml, 107.7 mmol) was added dropwise to the mixture of 12-Hydroxydodecanoic acid benzyl ester (21 g, 71.8 mmol), triphenylphosphine (28.29 g, 107.7 mmol) and N-hydroxyphthalimide (12.88 g, 78.98 mmol) in absolute THF (250 ml) at −20°-−30° C. under stirring. The reaction mixture was stirred at this temperature for additional 2-3 h, after which time TLC (hexane-ethylacetate 3:1) indicated reaction completion. The solvent was removed in vacuo and the residue was treated ether (250 ml). Formed precipitate of triphenylphosphine oxide was filtered off, mother liquor was evaporated to dryness and the residue was dissolved in methylene chloride and purified by flash chromatography on silica gel in hexane-ethyl acetate (7:3). Appropriate fractions were pooled and evaporated to dryness to afford 26.5 g (84.4%) of compound 15.

후처리

  1. stirringThe reaction mixture was stirred at this temperature for additional 2-3 h
  2. customreaction completion
  3. customThe solvent was removed in vacuo
  4. additionthe residue was treated ether (250 ml)

출처 및 근거

ORD 기록
ord-c14fee49e0b14b92af72a16dd5b0381a
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07833992B2

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