Methyl formate → HCID 70625426, compound

HRID 866396Notes

Reaction equation

HRID 866396 reaction equation
C([O:3][CH3:4])=O.[CH3:5][C:6]1([C:13](=O)[CH3:14])[CH2:9][C:8]2([CH2:12][CH2:11][CH2:10]2)[CH2:7]1.[H-].[Na+]>CCOCC.CO>[CH3:5][C:6]1([CH:13]([CH:14]=[CH:4][OH:3])[CH2:14][CH2:13][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:9][C:8]2([CH2:12][CH2:11][CH2:10]2)[CH2:7]1

Participants

6

Reactant 3

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 20320778HCID 20320778, compound

Product 1

HCID 70625426HCID 70625426, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 7.8 g (130.0 mmol) methyl formate and 4.91 g (32.4 mmol) of 2-methyl-2-acetylspiro[3.3]heptane in 8.0 ml of dry ether was dropped into a slurry of 1.2 g of sodium hydride in 180 ml of ether. A few drops of MeOH were added and the reaction mixture stirred for 1.5 hr at 25° C. The reaction mixture was cooled to -10° C and the reaction quenched by slow addition of water. The layers were separated and the aqueous layer extracted twice with ether. The combined organic extracts were washed with water and 1 N NaOH. The combined aqueous layers were acidified with 6 N HCl and extracted with ether. The ether extracts were washed with brine, then dried (MgSO4), filtered and evaporated in vacuo to yield 4.0 g of (2-methylspiro[3.3]hept-2-yl)(2-hydroxyvinyl)heptane as a yellow oil (69.5%).

Workup

  1. temperatureThe reaction mixture was cooled to -10° C
  2. customthe reaction quenched by slow addition of water
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted twice with ether
  5. washThe combined organic extracts were washed with water and 1 N NaOH
  6. extractionextracted with ether
  7. washThe ether extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-0aaf0861a906482db31f072edb4cc6e5
Source dataset
uspto-grants-1978_07
Patent number
US04098823

Reaction notes

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