Ethyl Acetate → HCID 66828188, compound

HRID 714251Notes

Reaction equation

HRID 714251 reaction equation
CC(C)([O-])C.[K+].[C:7]1([C:13]2([CH2:19][CH:20]=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:22][CH2:23][O:24][C:25]([CH3:27])=[O:26]>C1COCC1>[C:7]1([C:13]2([CH2:19]/[CH:20]=[CH:27]/[C:25]([O:24][CH2:23][CH3:22])=[O:26])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 866882032-(1-Phenylcyclohexyl)acetaldehyde

Product 1

HCID 66828188HCID 66828188, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of triethyl phosphonoacetate (0.601 mL, 3.00 mmol) in THF (10 mL) at 0° C. was added 1 M potassium tert-butoxide (3.00 mL, 3.00 mmol) in THF dropwise and the mixture was stirred for 30 mins at the same temperature. Then a solution of 2-(1-phenylcyclohexyl)acetaldehyde (405 mg, 2 0 mmol) in 4 ml of THF was added dropwise and the mixture was stirred for 0.5 hrs at 0° C. and for 1.5 hrs at room temperature. The mixture was added to EtOAc and washed with water (2×) and saturated NH4Cl. The resulting material was dried over Na2SO4 and evaporated to give an oily residue. It was purified by Combiflash (80 g silica gel) eluting with 5:95 EtOAc-hexane to give (E)-ethyl 4-(1-phenylcyclohexyl)but-2-enoate (213.7 mg). 1H NMR (400 MHz, CDCl3) δ ppm 7.27-7.37 (4 H, m), 7.15-7.23 (1 H, m), 6.60 (1 H, ddd, J=15.49, 7.91, 7.80 Hz), 5.66 (1 H, dt, J=15.60, 1.32 Hz), 4.12 (2 H, q, J=7.18 Hz), 2.39 (2 H, dd, J=7.80, 1.21 Hz), 2.11 (2 H, dd, J=13.07, 5.60 Hz), 1.33-1.66 (8 H, m), 1.24 (3 H, t, J=7.18 Hz).

Workup

  1. stirringthe mixture was stirred for 0.5 hrs at 0° C. and for 1.5 hrs at room temperature
  2. washwashed with water (2×) and saturated NH4Cl
  3. dry with materialThe resulting material was dried over Na2SO4
  4. customevaporated
  5. customto give an oily residue
  6. customIt was purified by Combiflash (80 g silica gel)
  7. washeluting with 5:95 EtOAc-hexane

Sources & evidence

ORD record
ord-7260e41bec9c4e85900c7c1bb4579ad7
Source dataset
uspto-grants-2015_11
Patent number
US09187437B2

Reaction notes

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