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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
Notes
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Reaction equation

HRID 1086065 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent2×

Procedure

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 ;

Workup

  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

Sources & evidence

ORD record
ord-facfd26347cf4bd6b0607a1209ee49e2
Source dataset
uspto-grants-1991_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05011947

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes