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Tert-butyl acetoacetate → 1,1-Dimethylethyl 9,9-bis(4-fluorophenyl)-5-hydroxy-8-(1-methylethyl)-3-oxo-6,8-nonadienoate

HRID 1086065
ノート
印刷プレビュー

反応式

HRID 1086065 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[C:9]([CH:14]([CH3:16])[CH3:15])[CH:10]=[CH:11][CH:12]=[O:13])=[CH:4][CH:3]=1.[C:24]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:29])[CH2:25][C:26]([CH3:28])=[O:27].[H-].[Na+].C([Li])CCC>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)=[C:9]([CH:14]([CH3:16])[CH3:15])[CH:10]=[CH:11][CH:12]([OH:13])[CH2:28][C:26](=[O:27])[CH2:25][C:24]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 15538Tert-butyl acetoacetate2 回HCID 24758Sodium hydrideHCID 538739495,5-Bis(4-fluorophenyl)-4-(1-methylethyl)-2,4-pentadienalHCID 178418339Butyllithium

生成物 1

HCID 537261511,1-Dimethylethyl 9,9-bis(4-fluorophenyl)-5-hydroxy-8-(1-methylethyl)-3-oxo-6,8-nonadienoate収率 66.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 5,5-bis(4-fluorophenyl)-4-(1-methyl-ethyl)-2,4-pentadienal (0.5 g, 1.6 mmol) in 20 mL tetrahydrafuran at -70° C., was added the dianion of t-butyl acetoacetate (2.1 mL of 1M solution in THF, 2.1 mmol) which was prepared by adding t-butyl acetoacetate (4.0 g, 25 mmol) in 4 mL tetrahydrofuran to a suspension of sodium hydride (1.0 g of 50% in oil, 25 mmol) in 6 mL tetrahydrofuran at -10° C., butyl lithium (11.4 mL of 2.2M solution) 25 mL was added and stirred for 0.5 hrs. After stirring for 2.5 hrs. the reaction was quenched with 2N hydrochloric acid. The mixture was extracted with diethyl ether. The extracts were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 1% methanol in methylene chloride to give 0.5 g of the title compound as a clear oil. MS(CI): m/e =370 for M3 ;

後処理

  1. customwas prepared
  2. stirringAfter stirring for 2.5 hrs
  3. customthe reaction was quenched with 2N hydrochloric acid
  4. extractionThe mixture was extracted with diethyl ether
  5. dry with materialThe extracts were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel eluting with 1% methanol in methylene chloride

出典と根拠

ORDレコード
ord-facfd26347cf4bd6b0607a1209ee49e2
出典データセット
uspto-grants-1991_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05011947

反応ノート

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