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Triphenylphosphine → HCID 10886037、化合物

HRID 1741854
ノート
印刷プレビュー

反応式

HRID 1741854 の反応式
[OH:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]3)=[O:7])=[CH:4][CH:3]=1.[CH2:27]([C:31]1[CH:36]=[CH:35][C:34]([C@H:37](O)[CH2:38][CH2:39][CH3:40])=[CH:33][CH:32]=1)[CH:28]([CH3:30])[CH3:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C1(C)C=CC=CC=1.C(O)(=O)C>[CH2:27]([C:31]1[CH:32]=[CH:33][C:34]([C@@H:37]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([C:8]3[CH:9]=[C:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:11]4[C:16]=3[CH:15]=[CH:14][CH:13]=[CH:12]4)=[O:7])=[CH:25][CH:26]=2)[CH2:38][CH2:39][CH3:40])=[CH:35][CH:36]=1)[CH:28]([CH3:30])[CH3:29]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11063606HCID 11063606、化合物HCID 11824313Ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrate

生成物 1

HCID 10886037HCID 10886037、化合物収率 49%

試薬・触媒・溶媒 3

HCID 176
Acetic Acid
溶媒
HCID 1140Toluene溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

To a mixture of ethyl 4-[1-(4-hydroxybenzoyl)indolizin- 3-yl]butyrate (392 mg), (R)-1-(4-isobutylphenyl)butan-1-ol (230 mg) and triphenylphosphine (292 mg) in tetrahydrofuran (3 ml) and toluene (15 ml) was added diethyl azodicarboxylate (0.178 ml) at -20° C. under nitrogen atmosphere. After the mixture was stirred at -20° C. under nitrogen for 2.5 hours, acetic acid (0.05 ml) was added and the mixture was warmed up to room temperature. The solvent was evaporated under reduced pressure and the residue was poured into a mixture of ethyl acetate and water. The organic phase was separated, washed with water and brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel column eluting with a mixture of n-hexane and ethyl acetate (4:1) to give ethyl 4-[1-[4-[(S)-1-(4-isobutylphenyl)butoxy]benzoyl]indolizin-3-yl]butyrate (295 mg) as an oil.

後処理

  1. temperaturethe mixture was warmed up to room temperature
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe residue was poured into a mixture of ethyl acetate and water
  4. customThe organic phase was separated
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel column
  9. washeluting with a mixture of n-hexane and ethyl acetate (4:1)

出典と根拠

ORDレコード
ord-c9ae443382ea4d5a80d8cd5dab459ae9
出典データセット
uspto-grants-1994_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05334716

反応ノート

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