Tert-butyl acetoacetate → tert-Butyl 9,9-bis(2-fluoro-4-methylphenyl)-5-hydroxy-8-(1-methyl-1H-tetrazol-5-yl)-3-oxo-6,8-nonadienoate

HRID 330680Notes

Reaction equation

HRID 330680 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[F:28])=[C:10]([C:15]1[N:19]([CH3:20])[N:18]=[N:17][N:16]=1)[CH:11]=[CH:12][CH:13]=[O:14].[C:29]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])(=[O:34])[CH2:30][C:31]([CH3:33])=[O:32]>O1CCCC1>[F:28][C:22]1[CH:23]=[C:24]([CH3:27])[CH:25]=[CH:26][C:21]=1[C:9]([C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[F:1])=[C:10]([C:15]1[N:19]([CH3:20])[N:18]=[N:17][N:16]=1)[CH:11]=[CH:12][CH:13]([OH:14])[CH2:33][C:31](=[O:32])[CH2:30][C:29]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]

Participants

4

Reactant 2

HCID 15538Tert-butyl acetoacetateHCID 542073765,5-Bis(2-fluoro-4-methylphenyl)-4-(1-methyl-1H-tetrazol-5-yl)-2,4-pentadienal

Product 1

HCID 54055970tert-Butyl 9,9-bis(2-fluoro-4-methylphenyl)-5-hydroxy-8-(1-methyl-1H-tetrazol-5-yl)-3-oxo-6,8-nonadienoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5,5-bis(2-fluoro-4-methylphenyl)-4-(1-methyl-1H-tetrazol-5-yl)-2,4-pentadienal (1.3 g, 3.4 mmoles) in tetrahydrofuran (15 mL) at -50 ° C. was added the dianion of t-butyl acetoacetate (3.4 mL of a 1M solution, 3.4 mmoles). After stirring for 2 hours, another 0.7 mL of dianion solution was added and the solution stirred for an additional hour. The reaction was quenched with 1N hydrochloric acid and the mixture extracted with methylene chloride. The extracts were dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel eluting with 1% (v/v) methanol in methylene chloride to give 1.3 g of the title compound; m.p.=55°-63° C.

Workup

  1. additionanother 0.7 mL of dianion solution was added
  2. stirringthe solution stirred for an additional hour
  3. customThe reaction was quenched with 1N hydrochloric acid
  4. extractionthe mixture extracted with methylene chloride
  5. dry with materialThe extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel eluting with 1% (v/v) methanol in methylene chloride

Sources & evidence

ORD record
ord-ed087bbc33d148d4a60f79083939c96e
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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