Ethanol → HCID 58380816, compound

HRID 1948143Notes

Reaction equation

HRID 1948143 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([O:17][CH3:18])([C:15]#[N:16])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([Mg]Br)[CH3:20].C(O)C>C1(C)C=CC=CC=1>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([CH:15]([NH2:16])[CH2:19][CH3:20])([O:17][CH3:18])[CH2:11][CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 16083429HCID 16083429, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 58380816HCID 58380816, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under argon, 1.2 g of 39 were dissolved in 60 mL of absolute toluene. Then, 2.9 mL of ethylmagnesium bromide (3M in diethylether) were added dropwise. The mixture was allowed to warm to room temperature. After conversion was complete, the reaction mixture was cooled to 5° C. and 2 mL of dry ethanol were added. The mixture was filtered over celite and the filter cake was washed with tetrahydrofuran. Volatiles were removed in vacuo, the residue was dissolved in 20 mL of dry ethanol, 331 mg of sodium borohydride were added and the mixture was stirred for 2 h at 0° C. The mixture was evaporated, 20 mL of methyl tert.butyl ether and 20 mL of water were added and 1N aqueous hydrochloric acid was added dropwise until gas evolution ceased. The organic layer was separated, washed with brine, dried and evaporated to give 1 g of the desired product as a cis/trans mixture. Rt=0.96/0.99 min (Method M). Detected mass: 278.3 (M+H+).

Workup

  1. temperaturethe reaction mixture was cooled to 5° C.
  2. filtrationThe mixture was filtered over celite
  3. washthe filter cake was washed with tetrahydrofuran
  4. customVolatiles were removed in vacuo
  5. dissolutionthe residue was dissolved in 20 mL of dry ethanol
  6. addition331 mg of sodium borohydride were added
  7. customThe mixture was evaporated
  8. addition20 mL of methyl tert.butyl ether and 20 mL of water were added
  9. addition1N aqueous hydrochloric acid was added dropwise until gas evolution
  10. customThe organic layer was separated
  11. washwashed with brine
  12. customdried
  13. customevaporated

Sources & evidence

ORD record
ord-45b2c762493f44a0b2ea6b3568d16f91
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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