Solketal → HCID 22174536, compound

HRID 1797279Notes

Reaction equation

HRID 1797279 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[CH2:13]/[CH:14]=[CH:15]/[Sn:16]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20]>CN(C=O)C>[CH2:25]([Sn:16]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])/[CH:15]=[CH:14]/[CH2:13][O:10][CH2:9][CH:7]1[CH2:6][O:5][C:4]([CH3:11])([CH3:3])[O:8]1)[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 7528SolketalHCID 24758Sodium hydrideHCID 10905679167288-95-1

Product 1

HCID 22174536HCID 22174536, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Sodium hydride (215 mg) was added to a solution of (2,2-dimethyl-1,3-dioxolan-4-yl)methanol (644 mg) in dry DMF (25 mL) at 0° C. [(1E)-3-bromoprop-1-enyl](tributyl)stannane (1.00 g) was added to the reaction mixture after 10 min. The reaction mixture was stirred for 20 h at 20° C. and then quenched with saturated NH4Cl (aq.). Extraction with EtOAc and drying (Na2SO4) of the organic phase gave, after concentration in vacuo, the crude product. Purification was done by chromatography eluting with petroleum ether/EtOAc 10:1 to afford the title compound as a liquid.

Workup

  1. additionwas added to the reaction mixture after 10 min
  2. customquenched with saturated NH4Cl (aq.)
  3. extractionExtraction with EtOAc
  4. dry with materialdrying (Na2SO4) of the organic phase
  5. customgave
  6. concentrationafter concentration in vacuo
  7. customPurification
  8. washeluting with petroleum ether/EtOAc 10:1

Sources & evidence

ORD record
ord-34b9a11e67a54d07b4d8f329cf020fed
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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