Ethyl formate → HCID 86645767, compound

HRID 1676110Notes

Reaction equation

HRID 1676110 reaction equation
C[C:2]([O-:5])(C)C.[K+].C(OC=O)C.[CH3:12][CH:13]([C:15](=[O:21])[CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH3:14]>C1COCC1.C(OCC)C>[OH:5][CH:2]=[C:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:15](=[O:21])[CH:13]([CH3:14])[CH3:12]

Participants

6

Reactant 3

HCID 8025Ethyl formate2×HCID 881492,6-Dimethylheptan-3-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 86645767HCID 86645767, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

To a solution of KOtBu (15.6 g, 139 mmol) in THF (200 mL) is added ethylformate (27.4 g, 370 mmol). During the addition, the mixture is cooled with a water bath to 10° C. Strong gas evolution occurs. The mixture is stirred until the gas evolution ceases (5 min) and is then cooled to −5° C. To this mixture a solution of 2,6-dimethyl-heptan-3-one (20 g, 141 mmol) and ethylformate (13.7 g, 185 mmol) in THF (20 mL) is added slowly during 30 min. The reaction mixture is stirred for 2 h and allowed to slowly warm to rt. The reaction is diluted with diethyl ether (200 mL) and washed with 1 N aq. HCl (2×100 mL). The organic extract is dried (Na2SO4), filtered and evaporated to give 1-hydroxy-2-isobutyl-4-methyl-pent-1-en-3-one (7.35 g) as a brown resin; LC-MS: tR=0.91 min, [M+1]=171.21.

Workup

  1. additionDuring the addition
  2. temperatureis then cooled to −5° C
  3. stirringThe reaction mixture is stirred for 2 h
  4. temperatureto slowly warm to rt
  5. washwashed with 1 N aq. HCl (2×100 mL)
  6. extractionThe organic extract
  7. dry with materialis dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-77b137fb89644fb48445fc5a5700abc7
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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