2-Naphthalenecarboxaldehyde → HCID 13105363, 화합물

HRID 365132

반응식

HRID 365132 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 13105363HCID 13105363, 화합물

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3ad2552c093947eba337459f5871f91e
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04608390

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