Trimethylsilylacetylene → 1044277-44-2

HRID 2422488Notes

Reaction equation

HRID 2422488 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Li])CCC.[O:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1>C1COCC1>[CH3:1][Si:2]([C:5]#[C:6][C:15]1([OH:18])[CH2:16][CH2:17][O:12][CH2:13][CH2:14]1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 121599Tetrahydro-4H-pyran-4-oneHCID 178418339Butyllithium

Product 1

HCID 597748681044277-44-2

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trimethylsilylacetylene (5 mL, 35.4 mmol) in THF (100 mL) cooled at −78° C., a 1.6M n-butyllithium in hexanes (22.1 mL, 35.4 mmol) was added dropwise. The solution was stirred for 30 min before tetrahydro-4H-pyran-4-one (3.47 mL, 37.2 mmol) was added. The temperature was slowly raised to room temperature and the reaction was stirred overnight. The reaction was quenched with a saturated ammonium chloride solution and the aqueous layer was extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue obtained was used as such for the next step. 1H NMR (400 MHz, acetone-d6): 4.60 (s, 1H), 3.85-3.75 (m, 2H), 3.61-3.51 (m, 2H), 1.98-1.87 (m, 2H), 1.74-1.66 (m, 2H), 0.16 (s, 9H).

Workup

  1. additionwas added
  2. customThe reaction was quenched with a saturated ammonium chloride solution
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6742ab907ec7466491b7741ba8f7ddfe
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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