Butyl oxoacetate → HCID 54056081, compound

HRID 1647930Notes

Reaction equation

HRID 1647930 reaction equation
[CH3:1][Si:2]([CH3:10])([CH3:9])[O:3]/[C:4](/[CH2:7][CH3:8])=[CH:5]\[CH3:6].[C:11]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:14])[CH:12]=[O:13].C(=O)([O-])O.[Na+]>C(Cl)Cl>[OH:13][CH:12]([CH:7]([CH3:8])[C:4]([O:3][Si:2]([CH3:10])([CH3:9])[CH3:1])=[CH:5][CH3:6])[C:11]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14]

Participants

5

Reactant 3

HCID 80521Butyl oxoacetateHCID 516892Sodium BicarbonateHCID 10986519HCID 10986519, compound

Product 1

HCID 54056081HCID 54056081, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 21.6 mg (0.05 mmol) of a chiral titanium complex, (R)-1, in 3 ml of methylene chloride were added 157 mg (1 mmol) of Z-3-(trimethylsilyl)oxy-2-pentene and subsequently a solution of 130 mg (1 mmol) of freshly distilled butyl glyoxylate in 0.5 ml of methylene chloride at 0° C. After stirring for 30 minutes at that temperature, the resultant mixture was poured into 10 ml of a saturated sodium hydrogencarbonate aqueous solution at 0° C. The solution was filtered through a pad of Celite, and the filtrate was extracted three times with a 5 ml portion of diethyl ether. The combined organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. Separation by silica gel chromatography (eluent: hexane/ethyl acetate=15/1 by volume) gave 181 mg (0.63 mmol; yield 63%) of butyl 2-hydroxy-3-methyl-4-(trimethylsilyl)oxy-4-hexenoate.

Workup

  1. customat 0° C
  2. filtrationThe solution was filtered through a pad of Celite
  3. extractionthe filtrate was extracted three times with a 5 ml portion of diethyl ether
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customSeparation by silica gel chromatography (eluent: hexane/ethyl acetate=15/1 by volume)

Sources & evidence

ORD record
ord-2d880811dd60451ab96388c8c46c0713
Source dataset
uspto-grants-1995_07
Patent number
US05434289

Reaction notes

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