Solketal → HCID 90303257, compound

HRID 1051963Notes

Reaction equation

HRID 1051963 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:11])[O:8][CH:7]([CH2:9][OH:10])[CH2:6][O:5]1.Br[C:13]1[N:14]=[CH:15][S:16][CH:17]=1>>[CH3:3][C:4]1([CH3:11])[O:8][CH:7]([CH2:9][O:10][C:13]2[N:14]=[CH:15][S:16][CH:17]=2)[CH2:6][O:5]1

Participants

4

Reactant 3

HCID 7528SolketalHCID 24758Sodium hydrideHCID 27632184-Bromothiazole

Product 1

HCID 90303257HCID 90303257, compound

Procedure

NaH (60% dispersion in mineral oil, 12.19 g, 305.3 mmol) was added portionwise to DL-1,2-isopropylideneglycerol (16.11 g, 1218 mmol) and the mixture was stirred until gas evolution had ceased (ca. 30 min RT, followed by 2 h at 60° C.). Subsequently, 4-bromothiazole (20.00 g, 121.9 mmol) was added and the mixture was stirred at 140° C. for 45 min. Subsequently, the reaction mixture was quenched with aq. sat. NH4Cl and extracted with EtOAc. The comb. org. layers were washed with brine, dried over MgSO4, and conc. in vacuo. The residue was subjected to distillation and the volatiles (HV, 60° C.) were removed. The residue was purified by means of CC (5-40% EtOAc/Hept) to provide a yellow oil.

Workup

  1. custom(ca. 30 min RT, followed by 2 h at 60° C.)
  2. stirringthe mixture was stirred at 140° C. for 45 min
  3. customSubsequently, the reaction mixture was quenched with aq. sat. NH4Cl
  4. extractionextracted with EtOAc
  5. washlayers were washed with brine
  6. dry with materialdried over MgSO4
  7. distillationThe residue was subjected to distillation
  8. customthe volatiles (HV, 60° C.) were removed
  9. customThe residue was purified by means of CC (5-40% EtOAc/Hept)
  10. customto provide a yellow oil

Sources & evidence

ORD record
ord-409030ba4bea4eafa4e87de9e6c61d70
Source dataset
uspto-grants-2016_07
Patent number
US09388198B2

Reaction notes

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