Triethyl orthoacetate → HCID 57672468, compound

HRID 2101793Notes

Reaction equation

HRID 2101793 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C@@H:11](O)[CH3:12])=[C:5]([CH3:14])[CH:4]=1.[C:15](OCC)([O:20]CC)([O:17][CH2:18][CH3:19])[CH3:16]>C(O)(=O)CC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9](/[CH:10]=[CH:11]/[CH3:12])[CH2:16][C:15]([O:17][CH2:18][CH3:19])=[O:20])=[C:5]([CH3:14])[CH:4]=1

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 57672504HCID 57672504, compound

Product 1

HCID 57672468HCID 57672468, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidCatalyst

Conditions

Temperature
155 °C

Procedure

To a stirred solution of (S,E)-4-(4-methoxy-2-methylphenyl)but-3-en-2-ol 28.5 (2.00 g, 10 mmol) (99% ee) in triethyl orthoacetate (20 mL, 109 mmol) at 23° C. was added propanoic acid (0.01 mL, 0.1 mmol). The reaction mixture was heated to 155° C., and stirred for 24 hours. The reaction was cooled to room temperature and concentrated in vacuo. The resulting product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford compound (S,E)-ethyl 3-(4-methoxy-2-methylphenyl)hex-4-enoate 28.6 (1.22 g, 45% yield) as a clear oil. MS ESI (pos.) m/e: 280.1 (M+H2O), 263.1 (M+H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe resulting product was purified by silica gel flash chromatography (0-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-c64ea997583d41e0b756234b77fb7f23
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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