Phthalimide → 2-[4-(1-Hydroxy-1-methyl-ethyl)-cyclohex-1-enylmethyl]-isoindole-1,3-dione

HRID 844021ノート

反応式

HRID 844021 の反応式
O[CH2:2][C:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:12])([CH3:11])[CH3:10])[CH2:5][CH:4]=1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[OH:12][C:9]([CH:6]1[CH2:7][CH2:8][C:3]([CH2:2][N:17]2[C:13](=[O:23])[C:14]3[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16]2=[O:18])=[CH:4][CH2:5]1)([CH3:11])[CH3:10]

参加物

5

反応物 3

HCID 6809PhthalimideHCID 1106624-(2-Hydroxy-2-propyl)cyclohexene-1-methanolHCID 5363146Diisopropyl azodicarboxylate

生成物 1

HCID 226124142-[4-(1-Hydroxy-1-methyl-ethyl)-cyclohex-1-enylmethyl]-isoindole-1,3-dione収率 55.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 2-(4-Hydroxymethyl-cyclohex-3-enyl)-propan-2-ol (5.765 grams, 34.270 mmole), Phthalimide (6.50 grams, 44.208 mmole), and triphenyl phosphene (11.60 grams, 44.208 mmole) in tetrahydrofuran (200 ml) at room temperature was added DIAD (9.010 grams, 44.552 mmole) dropwise, and the peach mixture was stirred at room temperature over night. The mixture was quenched with 150 ml water and extracted with 2×100 ml ethyl acetate. It was then concentrated to a yellow residue. This was taken up in diethyl ether, diluted with hexane, chilled and filtered. The crude product was purified via flash chromatography on silica using 50% ethyl acetate/hexane as eluent to give a yellow gum (5.73 g). MW 299.373; MS (m/e) 279 (M+−18).

後処理

  1. customThe mixture was quenched with 150 ml water
  2. extractionextracted with 2×100 ml ethyl acetate
  3. concentrationIt was then concentrated to a yellow residue
  4. additiondiluted with hexane
  5. temperaturechilled
  6. filtrationfiltered
  7. customThe crude product was purified via flash chromatography on silica using 50% ethyl acetate/hexane as eluent

出典と根拠

ORDレコード
ord-14aec06fc791440e93fb4fc822329a46
出典データセット
uspto-grants-2002_04
特許番号
US06380218B1

反応ノート

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