(5-Carboxypentyl)triphenylphosphanium bromide → HCID 53684295、化合物

HRID 367306

反応式

HRID 367306 の反応式
CC(C)([O-])C.[K+].[Br-].[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:10])=[O:9].[C:35]([C:39]1[C:44]2[CH2:45][C:46](C=O)([CH3:48])[O:47][C:43]=2[CH:42]=[C:41]([C:51]([CH3:54])([CH3:53])[CH3:52])[C:40]=1[O:55][Si](C)(C)C)([CH3:38])([CH3:37])[CH3:36]>C1COCC1>[C:35]([C:39]1[C:44]2[CH2:45][C:46]([CH:15]=[CH:14][CH2:13][CH2:12][CH2:11][C:8]([OH:10])=[O:9])([CH3:48])[O:47][C:43]=2[CH:42]=[C:41]([C:51]([CH3:54])([CH3:53])[CH3:52])[C:40]=1[OH:55])([CH3:38])([CH3:37])[CH3:36]

参加物

5

反応物 3

HCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 23288036HCID 23288036、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 53684295HCID 53684295、化合物収率 43%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

Under a nitrogen atmosphere, a solution of 0.92 g of potassium t-butoxide in 10 ml of THF was added dropwise to a suspension of 0.46 g of 5-carboxypentyltriphenylphosphonium bromide in 5 ml of THF at 0° C., and the mixture was stirred for 30 minutes. To the reaction solution was added dropwise a solution of 4,6-di-t-butyl-2-formyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran synthesized in Example 72-2) in 10 ml of THF, and the mixture was stirred overnight while slowly warming to room temperature. The reaction solution was extracted with water and diethyl ether, and the combined aqueous layers were acidified with concentrated hydrochloric acid and extracted with diethyl ether. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography eluting with n-hexane containing 50% ethyl acetate to give 0.22 g of 6-(4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)-5-hexenoic acid as a colorless viscous liquid (yield 43%).

後処理

  1. stirringthe mixture was stirred overnight
  2. extractionThe reaction solution was extracted with water and diethyl ether
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with n-hexane containing 50% ethyl acetate

出典と根拠

ORDレコード
ord-9301289ae4924d06bc13c186d034667f
出典データセット
uspto-grants-2000_10
特許番号
US06133279

関連ノート

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