2-Naphthalenecarboxaldehyde → HCID 13105363、化合物

HRID 365132ノート

反応式

HRID 365132 の反応式
[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])C=CC=CC=1.[CH:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1[CH:39]=O.CC(C)([O-])C.[K+]>CS(C)=O>[CH:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1/[CH:39]=[CH:10]\[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

参加物

5

反応物 3

HCID 62012-NaphthalenecarboxaldehydeHCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 13105363HCID 13105363、化合物

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Triphenyl (5-carboxypentyl)phosphonium bromide (937 mg, 2.1 mmole) and 2-napthaldehyde (300 mg, 1.92 mmole) were dissolved in DMSO (50 mL, freshly distilled from CaH2) and potassium t-butoxide (540 mg, 4.8 mmole) was added. After stirring for 30 minutes the reaction was quenched with saturated NH4Cl solution (25 mL) and poured into ether. The ether layer was dried with saturated NaCl and MgSO4 and the solvent was evaporated. The resulting 1:1 mixture E/Z isomers were separated with flash chromatography eluting with ether/hexane/formic acid (10:89:1).

後処理

  1. additionwas added
  2. customwas quenched with saturated NH4Cl solution (25 mL)
  3. additionpoured into ether
  4. dry with materialThe ether layer was dried with saturated NaCl and MgSO4
  5. customthe solvent was evaporated
  6. customThe resulting 1:1 mixture E/Z isomers were separated with flash chromatography
  7. washeluting with ether/hexane/formic acid (10:89:1)

出典と根拠

ORDレコード
ord-3ad2552c093947eba337459f5871f91e
出典データセット
uspto-grants-1986_08
特許番号
US04608390

反応ノート

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