Methyl vinyl ketone → 2-(Trimethylsiloxy)-1,3-butadiene

HRID 1267839Notes

Reaction equation

HRID 1267839 reaction equation
[CH3:1][C:2](=[O:5])[CH:3]=[CH2:4].C(N(CC)CC)C.[CH3:13][Si:14](OS(C(F)(F)F)(=O)=O)([CH3:16])[CH3:15]>C(Cl)Cl>[CH3:13][Si:14]([CH3:16])([CH3:15])[O:5][C:2]([CH:3]=[CH2:4])=[CH2:1]

Participants

5

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 8471TriethylamineHCID 65367Trimethylsilyl triflate

Product 1

HCID 5546572-(Trimethylsiloxy)-1,3-butadiene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

70 μl (0.86 mmoles) of 3-buten-2-one [compound of formula 5 wherein R1 ═R2═R6═H] and 2 ml of anhydrous CH2Cl2 are charged, at 0° C. under argon in a two-necked round bottom flask equipped with magnetic stirrer and dropping funnel. 170 μl (1.22 mmoles) of triethylamine (distilled on KOH) and 209 μl (1.08 mmoles) of trimethylsilyltrifluorometansulphonate (TMDOTf) (drop by drop) are added to the mixture. In this conditions 2 -(trimethylsilyloxy)-1,3-butadiene [compound 6 wherein R1 =R2═R6═H] is formed “in situ”. The mixture is stirred for 45 minutes and thereafter a solution of 100 mg (0.36 mmoles) of the product from Example 2 in 2 ml of anhydrous CH2Cl2 is added therein, drop by drop, together with 69 μl (0.36 mmoles) of TMSOTf. The mixture is brought to room temperature and after 30 minutes 4 ml of a saturated solution of NAHCO3 are added and the mixture is stirred vigorously for 36 h.

Workup

  1. customequipped with magnetic stirrer

Sources & evidence

ORD record
ord-9b650e97d7ae449394d338bb09f57ec6
Source dataset
uspto-grants-2003_04
Patent number
US06555549B2

Reaction notes

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