Sodium hydride → HCID 178486063, compound

HRID 630375Notes

Reaction equation

HRID 630375 reaction equation
[OH:1][C:2]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[C:3]([O:5][CH3:6])=[O:4].O[C@H]1[CH2:23][CH2:22][C@H:21]([N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]1.[H-].[Na+]>C1(C)C=CC=CC=1>[OH:1][C:2]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[C:3]([O:5][C@H:6]1[CH2:23][CH2:22][C@H:21]([N:24]([C:25]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:31])[CH3:32])[CH2:20][CH2:19]1)=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11414137Methyl alpha-hydroxy-alpha-2-thienyl-2-thiopheneacetateHCID 178486055HCID 178486055, compound2×

Product 1

HCID 178486063HCID 178486063, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
155 °C

Procedure

To a solution of methyl hydroxy(di-2-thienyl)acetate (5.8 g, 0.02 mol) (prepared according to Acta Chemica Scandinavica 24 (1970) 1590-1596) in anhydrous toluene (95 mL) was first added a solution of tert-butyl (trans-4-hydroxycyclohexyl)-methylcarbamate (intermediate 3; 6 g, 0.02 mol) in anhydrous toluene (95 mL) and secondly sodium hydride (60%, 0.45 g, 0.01 mol). After few minutes the mixture was warmed to 155° C. and the solvent was distilled and simultaneously replaced. This procedure was carried on during 1 hour and a half. The mixture was cooled to room temperature and diluted with ether (300 mL). The organic layer was washed with sodium bicarbonate 4% (2×200 mL) and brine, dried, filtered and evaporated over reduced pressure giving the title compound as a yellow solid (69%), which was used in the next step without further purification.

Workup

  1. distillationthe solvent was distilled
  2. customwas carried on during 1 hour
  3. temperatureThe mixture was cooled to room temperature
  4. additiondiluted with ether (300 mL)
  5. washThe organic layer was washed with sodium bicarbonate 4% (2×200 mL) and brine
  6. customdried
  7. filtrationfiltered
  8. customevaporated over reduced pressure

Sources & evidence

ORD record
ord-7436c803cbbe452885049419e4e00181
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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