Acetaldehyde → HCID 178472491, compound

HRID 2059988Notes

Reaction equation

HRID 2059988 reaction equation
CC([Si](C)(C)[O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]1)(C)C.[SiH](CC)(CC)[CH2:21][CH3:22].C(=O)C.C([O-])(O)=O.[Na+]>CC#N>[CH2:21]([O:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:12]1)[CH3:22]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 178472501HCID 178472501, compound

Product 1

HCID 178472491HCID 178472491, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

cis/trans Ethyl 4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}cyclohexanecarboxylate (D1, 35 g, 122 mmol) was dissolved in CH3CN (250 mL) and Et3SiH (1.2 eq., 146 mmol, 23 mL), BiBr3 (4% mol, 4.9 mmol, 2.2 g) were added portionwise at room temperature followed by acetaldehyde (1.2 eq., 8.2 mL) that was slowly added at 25° C. The mixture was stirred at room temperature for 1 hour. The mixture was subsequently poured onto an aqueous saturated solution of NaHCO3 and the mixture obtained was then extracted with EtOAc (3×). Organics were combined, washed with brine, dried over Na2SO4, filtered and the solvent was evaporated to afford the crude mixture that was purified by silica chromatography (Biotage 65i column, EtOAc-nhex) to afford the title compound, 21 g, 87%.

Workup

  1. additionwas slowly added at 25° C
  2. customthe mixture obtained
  3. extractionwas then extracted with EtOAc (3×)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customto afford the crude mixture that
  9. customwas purified by silica chromatography (Biotage 65i column, EtOAc-nhex)

Sources & evidence

ORD record
ord-a647147c61414a4c8693177db07b3e22
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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