Tetrahydrofuran → trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dione

HRID 128747

反応式

HRID 128747 の反応式
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.C(=O)(O)[O-].[Na+].C(N1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30])(OCC)=O.O1CCCC1>O>[C:21]1(=[O:30])[N:2]([CH:3]2[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]2)[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]12

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 31187N-CarbethoxyphthalimideHCID 516892Sodium BicarbonateHCID 522619(1s,4s)-4-Aminocyclohexan-1-ol hydrochloride

生成物 1

HCID 288726trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dione収率 72.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 4-aminocyclohexanol hydrochloride (6.08 g, 0.04 mole) in water (60 ml) was brought to pH 8 with aqueous sodium bicarbonate solution. N-carbethoxy-phthalimide (8.76 g, 0.04 mole) was added followed by tetrahydrofuran (until homogenous solution was obtained). The clear solution was stirred at room temperature overnight. During this time a white solid was precipitated. The tetrahydrofuran was removed in vacuo and the remaining aqueous solution was extracted with ethyl acetate until the solution was clear. The ethyl acetate extracts were combined, washed with water, dried (MgSO4) and concentrated to give 4-phthalimido cyclohexanol as a white solid (7.1 g).

後処理

  1. customDuring this time a white solid was precipitated
  2. customThe tetrahydrofuran was removed in vacuo
  3. extractionthe remaining aqueous solution was extracted with ethyl acetate until the solution
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-8ec7e128fb84498fa001bb7b74ba420b
出典データセット
uspto-grants-1995_11
特許番号
US05464864

関連ノート

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