Isobutyraldehyde → Methyl 2,2,4-trimethyl-3-trimethylsiloxyvalerate

HRID 544260

Reaction equation

HRID 544260 reaction equation
[C:1]([O-])(=[O:6])CCCC.[CH:8](=[O:12])[CH:9]([CH3:11])[CH3:10].CO[C:15]([O:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[C:16]([CH3:18])[CH3:17].C(OCC)(=O)C>O1CCCC1>[CH3:10][C:9]([CH3:11])([CH:15]([O:19][Si:20]([CH3:21])([CH3:22])[CH3:23])[CH:16]([CH3:17])[CH3:18])[C:8]([O:6][CH3:1])=[O:12]

Participants

6

Reactant 4

HCID 6561IsobutyraldehydeHCID 8857Ethyl AcetateHCID 114781ValerateHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-

Product 1

HCID 14763594Methyl 2,2,4-trimethyl-3-trimethylsiloxyvalerateYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In another preparation of the aforesaid valerate, isobutyraldehyde (0.72 g) was added to a mixture of [(1-methoxy-2-methyl-1-propenyl)oxy]trimethylsilane (1.74 g, 10 mmol) and (TAS)HF2 (100 mg, 0.1 mmol) in 20 mL of tetrahydrofuran under argon at -11°. The reaction mixture was stirred and the temperature was allowed to rise to 23°. Stirring was continued for 18 h and the mixture was then poured into 200 mL of ethyl acetate and extracted with water (200 mL), followed by washing with aqueous brine (200 mL). The organic layer was dried (MgSO4), filtered and evaporated in vacuo to give 2.39 g (97% yield) of methyl 2,2,4-trimethyl-3-trimethylsiloxyvalerate.

Workup

  1. customto rise to 23°
  2. stirringStirring
  3. extractionextracted with water (200 mL)
  4. washby washing with aqueous brine (200 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-bac238b4f8af48f1ab9eab24db71a069
Source dataset
uspto-grants-1984_05
Patent number
US04448980

Linked notes

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