(4-Carboxybutyl)triphenylphosphonium bromide → 6-(1,4-Dimethoxy-3-methylnaphthalen-2-yl)hex-5-enoic acid

HRID 2393183노트

반응식

HRID 2393183 반응식
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[C:5]([CH3:15])[C:4]=1[CH:16]=O.[Br-].[C:19]([CH2:22][CH2:23][CH2:24][CH2:25][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:21])=[O:20].CC(C)([O-])C.[K+]>CC(O)(C)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[C:5]([CH3:15])[C:4]=1[CH:16]=[CH:25][CH2:24][CH2:23][CH2:22][C:19]([OH:21])=[O:20]

참가 물질

5

반응물 3

HCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 128475291,4-Dimethoxy-3-methylnaphthalene-2-carbaldehydeHCID 23665647Potassium tert-butoxide

생성물 1

HCID 536355006-(1,4-Dimethoxy-3-methylnaphthalen-2-yl)hex-5-enoic acid수율 65.9%

시약·촉매·용매 1

HCID 22595558Toluene tert-butyl alcohol용매

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온도
60 °C

실험 절차

To a suspension of 1 g of 1,4-dimethoxy-3-methylnaphthalene-2-carbaldehyde and 3.85 g of (4-carboxybutyl)triphenylphosphonium bromide in 2.5% t-BuOH/toluene at 60° C. was added 1.95 g of potassium t-butoxide. The mixture was stirred at 60° C. for 30 min, extracted with 1N NaOH, and washed with toluene. The aqueous layer was neutralized with iN HCl until pH 4-5, then extracted with ethyl acetate. The organic layer was washed, dried, and concentrated, then the trsidue was purified with column chromatography over silica gel using n-hexane/ethyl acetate (2/1) as an eluent to give 0.9 g of the titled compound as an oil.

후처리

  1. extractionextracted with 1N NaOH
  2. washwashed with toluene
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed
  5. customdried
  6. concentrationconcentrated
  7. customthe trsidue was purified with column chromatography over silica gel

출처 및 근거

ORD 기록
ord-866a80352ea74365bab01d08ccdb5c2f
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05804601

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