Solketal → 13580-09-1

HRID 2377300Notes

Reaction equation

HRID 2377300 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[H-].[Na+].[CH2:12](Br)[C:13]#[CH:14]>C1COCC1.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-]>[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][O:8][CH2:14][C:13]#[CH:12])[CH2:4][O:3]1

Participants

6

Reactant 3

HCID 7528SolketalHCID 7842Propargyl bromideHCID 24758Sodium hydride

Product 1

HCID 342926213580-09-1

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 0° C. solution of (2,2-dimethyl-1,3-dioxolan-4-yl)methanol (Aldrich, 1 g) in THF (20 mL) was treated with NaH (327 mg, 60% oil dispersion), then refluxed for 60 min. The resulting suspension was cooled in an ice bath, treated with nBu4NI (55 mg) and propargyl bromide (0.9 mL) then stirred at r.t. for 2 h. The reaction was partitioned between water and ether (2×) and the combined ether extacts were dried (MgSO4), concentrated to give 1.3 g of the title compound. MS ESI(+) m/e 170.9 (M+H)+.

Workup

  1. temperaturerefluxed for 60 min
  2. temperatureThe resulting suspension was cooled in an ice bath
  3. customThe reaction was partitioned between water and ether (2×)
  4. dry with materialthe combined ether extacts were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7f2f0bd25f2947fc81309debf1665c86
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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