64776-06-3 → HCID 20320778, compound

HRID 866395Notes

Reaction equation

HRID 866395 reaction equation
[CH3:1][C:2]1([C:9]([OH:11])=O)[CH2:5][C:4]2([CH2:8][CH2:7][CH2:6]2)[CH2:3]1.[CH3:12][Li]>CCOCC>[CH3:1][C:2]1([C:9](=[O:11])[CH3:12])[CH2:3][C:4]2([CH2:6][CH2:7][CH2:8]2)[CH2:5]1

Participants

4

Reactant 2

HCID 2032077764776-06-3HCID 178418348HCID 178418348, compound

Product 1

HCID 20320778HCID 20320778, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 5.0 g (33.0 mmol) 2-methylspiro[3.3]heptane-2-carboxylic acid in 33.0 ml of dry ether was stirred under argon at 0° C and 47.6 ml (74.3 mmol) of 1.56 M methyl lithium in ether added dropwise. The reaction mixture was allowed to warm to 25° C and was stirred for 3.0 hr. The reaction mixture was cooled to -20° C and quenched by addition of 10% aqueous HCl. The layers were separated and the aqueous layer extracted with ether. The combined organic layers were washed with saturated aqueous sodium bicarbonate and brine, then dried (MgSO4), filtered, and evaporated in vacuo to afford 2-methyl-2-acetylspiro[3.3]heptane as a light yellow oil (4.91 g 98%).

Workup

  1. temperatureThe reaction mixture was cooled to -20° C
  2. customquenched by addition of 10% aqueous HCl
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with ether
  5. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-50122c90e0b540f0acefcad7db2d1dc0
Source dataset
uspto-grants-1978_07
Patent number
US04098823

Reaction notes

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