Triacetoxyperiodinane → 4-Benzyloxymethyl-cyclohexanecarbaldehyde

HRID 217237ノート

反応式

HRID 217237 の反応式
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH:16]=[O:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 22106763((1r,4r)-4-((Benzyloxy)methyl)cyclohexyl)methanol

生成物 1

HCID 186672404-Benzyloxymethyl-cyclohexanecarbaldehyde収率 79%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of (4-benzyloxymethyl-cyclohexyl)-methanol (1.40 g, 6 mmol) in dichloromethane 28 mL is added Dess-Martin periodinate (2.53 g, 6 mmol) at 0° C., and the mixture is stirred for 0.5 hour while warming to room temperature. After addition of saturated aqueous NaHCO3, the mixture is extracted with EtOAc. The combined organic layer after dried over MgSO4 is concentrated to obtain 4-benzyloxymethyl-cyclohexanecarbaldehyde as clear oil (1.07 g, 79%) after purification.

後処理

  1. extractionthe mixture is extracted with EtOAc
  2. dry with materialThe combined organic layer after dried over MgSO4
  3. concentrationis concentrated

出典と根拠

ORDレコード
ord-2d2e21fa5c6b4d67a39a03d48b0dabf2
出典データセット
uspto-grants-2012_06
特許番号
US08193349B2

反応ノート

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