Triethylsilane → Ethyl 4-[(cyclopropylmethyl)oxy]cyclohexanecarboxylate

HRID 2070098Notes

Reaction equation

HRID 2070098 reaction equation
C([SiH](CC)CC)C.CC([Si](C)(C)O[C@H]1CC[C@H](C(OCC)=O)CC1)(C)C.[Bi](Br)(Br)Br.C1(C=O)CC1.C([O-])(O)=O.[Na+].[CH:41]1([CH2:44][O:45][C@H:46]2[CH2:51][CH2:50][C@H:49]([C:52]([O:54][CH2:55][CH3:56])=[O:53])[CH2:48][CH2:47]2)[CH2:43][CH2:42]1>C(#N)C>[CH:41]1([CH2:44][O:45][CH:46]2[CH2:51][CH2:50][CH:49]([C:52]([O:54][CH2:55][CH3:56])=[O:53])[CH2:48][CH2:47]2)[CH2:42][CH2:43]1

Participants

8

Reactant 6

HCID 12052Triethylsilane2×HCID 82232bismuth(III) bromideHCID 123114CyclopropanecarboxaldehydeHCID 516892Sodium BicarbonateHCID 178472488HCID 178472488, compoundHCID 178472501HCID 178472501, compound

Product 1

HCID 59444059Ethyl 4-[(cyclopropylmethyl)oxy]cyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylsilane (10 mL, 63 mmol) was added to a solution of ethyl 4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}cyclohexanecarboxylate (D1, 13.6 g, 47.4 mmol), bismuth tribromide (923 mg, 2.06 mmol) and cyclopropanecarbaldehyde (4.25 mL, 56.8 mmol) in acetonitrile (60 mL) at rt under Ar. A black precipitate and an exotherm occurred on the addition of the triethylsilane. The mixture was stirred for 1 h before being poured on to sat. NaHCO3 (200 mL). The reaction was extracted with EtOAc (2×) and the combined organics were washed (sat. NaCl), dried (Na2SO4) and concentrated by rotary evaporation to give a mixture of cis and trans ethyl 4-[(cyclopropylmethyl)oxy]cyclohexanecarboxylate (D42, 20.8 g, 97%, contained silyl residues) as a colourless oil.

Workup

  1. extractionThe reaction was extracted with EtOAc (2×)
  2. washthe combined organics were washed (sat. NaCl)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by rotary evaporation
  5. customto give

Sources & evidence

ORD record
ord-883921ab032c4b71900ef9a473eb0aa5
Source dataset
uspto-grants-2012_10
Patent number
US08299257B2

Reaction notes

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