Propanal → HCID 178459257, compound

HRID 1968946Notes

Reaction equation

HRID 1968946 reaction equation
[CH:1](=[O:4])[CH2:2][CH3:3].CC([Si](C)(C)O[C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1)(C)C.[Bi](Br)(Br)Br.C([SiH](CC)CC)C>C(#N)C>[CH2:1]([O:4][C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 527PropanalHCID 12052TriethylsilaneHCID 82232bismuth(III) bromideHCID 178472501HCID 178472501, compound

Product 1

HCID 178459257HCID 178459257, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Propionaldehyde (6.4 g) in acetonitrile (50 mL) was added over 30 minutes to a solution of cis/trans ethyl 4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}cyclohexanecarboxylate (D1, 25.2 g), bismuth tribromide (4.4 g) and triethylsilane (17.5 mL) in acetonitrile (300 mL) and the mixture was stirred for a further 1.5 hours. The solvent was partially removed then the residue was treated with ethyl acetate and saturated sodium bicarbonate solution. The organic layer was separated, washed with brine, dried with anhydrous sodium sulphate and the solvent was removed to give the title compounds contaminated with silicone residues (39.1 g).

Workup

  1. customThe solvent was partially removed
  2. additionthe residue was treated with ethyl acetate and saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulphate
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-233e234679114ce8863c8491940f4efb
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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