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Acetyl chloride → 1-(4'-t-Butyldimethylsilyloxy-3'-methoxyphenyl)-1-hexene-3,5-dione

HRID 1650390
Notes
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Reaction equation

HRID 1650390 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17](=[O:19])[CH3:18])=[CH:11][C:10]=1[O:20][CH3:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].[C:30](Cl)(=[O:32])[CH3:31].C(OCC)C.CCCCCC>C1COCC1>[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17](=[O:19])[CH2:18][C:30](=[O:32])[CH3:31])=[CH:11][C:10]=1[O:20][CH3:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 2724682Lithium diisopropylamideHCID 21584099Diethylether hexaneHCID 545292101-(4'-t-Butyldimethylsilyloxy-3'-methoxyphenyl)-1-butene-3-one

Product 1

HCID 541564831-(4'-t-Butyldimethylsilyloxy-3'-methoxyphenyl)-1-hexene-3,5-dioneYield 34.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 1-(4'-t-butyldimethylsilyloxy-3'-methoxyphenyl)-1-butene-3-one (12.8 g, 41.8 mmol) in THF (50 mL) is cooled to -78° C. under an argon atmosphere. Lithium di-isopropyl amide (83.5 mmol, in 50 mL THF) is slowly added to the reaction mixture. The reaction is stirred at -78° C. for 30 minutes. Acetyl chloride (16.4 g, 209 mmol) dissolved in THF (20 mL) is then added to the reaction over a 30 minute period. The reaction is quenched with aqueous HCl. The layers are separated, and the aqueous layer is washed with ethyl acetate. The combined organic layers are washed with saturated aqueous sodium bicarbonate, dried over MgSO4, and evaporated to give a red oil. Flash chromatography (ethyl ether/hexane 2:8) afford 5.0 g (34%) of 1-(4'-t-butyldimethylsilyloxy-3'-methoxyphenyl)-1-hexene-3,5-dione, mp=81°-85° C.

Workup

  1. additionis then added to the reaction over a 30 minute period
  2. customThe reaction is quenched with aqueous HCl
  3. customThe layers are separated
  4. washthe aqueous layer is washed with ethyl acetate
  5. washThe combined organic layers are washed with saturated aqueous sodium bicarbonate
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customto give a red oil

Sources & evidence

ORD record
ord-bd9c0fd87dc9417d9668c4d6379a675e
Source dataset
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04924002

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes