Ethanol → Ethyl (3S)-3-(4-hydroxyphenyl)hex-4-ynoate

HRID 390388Notes

Reaction equation

HRID 390388 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:13]#[C:14][CH3:15])[CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([C:13]#[C:14][CH3:15])[CH2:9][C:10]([O:12][CH2:21][CH3:22])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 59855121(3S)-3-(4-Hydroxyphenyl)-4-hexynoic acid

Product 1

HCID 67087065Ethyl (3S)-3-(4-hydroxyphenyl)hex-4-ynoate

Procedure

To a 0° C. solution of (3S)-3-(4-hydroxyphenyl)hex-4-ynoic acid (2.7 g, 13.2 mmol) in ethanol (135 mL) is added sulfuric acid (2.7 mL) and the mixture is heated at reflux for 4 hours, concentrated, diluted with water, and extracted with EtOAc (2×100 mL). The combined extracts are washed with saturated brine, dried over sodium sulfate, filtered, and concentrated to yellow oil (2.1 g, 68%). 1H NMR (400 MHz, CDCl3) δ 7.23 (d, J=8.0 Hz, 2H), 6.76 (d, J=8.0 Hz, 2H), 4.9 (bs, 1H), 4.11 (q, J=6.8 Hz, 2H), 4.04 (m, 1H), 2.60-2.75 (m, 2H), 1.82 (s, 3H), 1.21 (t, J=6.8 Hz, 3H).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 4 hours
  3. concentrationconcentrated
  4. additiondiluted with water
  5. extractionextracted with EtOAc (2×100 mL)
  6. washThe combined extracts are washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to yellow oil (2.1 g, 68%)

Sources & evidence

ORD record
ord-9a5edba5ad724386a06db3a0d4534a46
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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