Water → Dibenzyl ether

HRID 36094

反応式

HRID 36094 の反応式
C(O[CH2:9][C@@H:10]1[C@@H:13]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][C:11]1=O)C1C=CC=CC=1.P(O)(O)O.O.[CH:29](O)(C)C>[Ir](Cl)(Cl)(Cl)Cl>[CH2:16]([O:15][CH2:14][C:13]1[CH:10]=[CH:9][CH:29]=[CH:11][CH:12]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

6

反応物 4

HCID 962WaterHCID 3776IsopropanolHCID 107909Phosphorous acidHCID 14863583(2S-trans)-2,3-bis[(benzyloxy)methyl]cyclobutanone

生成物 1

HCID 7657Dibenzyl ether

試薬・触媒・溶媒 1

HCID 24815Iridium tetrachloride触媒

実験手順

A mixture of (2S-trans)-2,3-bis[(benzyloxy)methyl]cyclobutanone (0.25 g., 0.806 mmole), iridium tetrachloride (0.016 g., 0.0483 mmole), phosphorous acid (0.397 g., 4.84 mmole) and water (0.3 ml.) in isopropanol (3 ml.) was refluxed overnight. The solvent was evaporated on a rotary evaporator. The residue was taken up in ethyl acetate and washed successively with 10% hydrochloric acid, brine, and 5% sodium bicarbonate. The organic layer was dried (magnesium sulfate) and the solvent was evaporated to give [1S-(1α,2β,3β)]-3-hydroxy-1,2-cyclobutanedimethanol, dibenzyl ether; TLC (40% ethyl acetate/hexane) Rf =0.51.

後処理

  1. temperaturewas refluxed overnight
  2. customThe solvent was evaporated on a rotary evaporator
  3. washwashed successively with 10% hydrochloric acid, brine, and 5% sodium bicarbonate
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-1ee0d42dc8654c73a17e61c3bd3a2269
出典データセット
uspto-grants-1995_05
特許番号
US05412134

関連ノート

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