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

HRID 2393183ノート

反応式

HRID 2393183 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 22595558Toluene tert-butyl alcohol溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-866a80352ea74365bab01d08ccdb5c2f
出典データセット
uspto-grants-1998_09
特許番号
US05804601

反応ノート

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