N-Hydroxyphthalimide → Triphenylphosphine Oxide

HRID 1172154ノート

反応式

HRID 1172154 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 13097Triphenylphosphine Oxide

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c14fee49e0b14b92af72a16dd5b0381a
出典データセット
uspto-grants-2010_11
特許番号
US07833992B2

反応ノート

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