Hydrochloric Acid → 343929-61-3

HRID 398089Notes

Reaction equation

HRID 398089 reaction equation
[S:1]1(=O)(=O)[C:5]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.CC(C[AlH]CC(C)C)C.CCO.Cl>C1(C)C=CC=CC=1.C1COCC1.O>[S:1]1[C:5]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14487Diisobutylaluminum hydrideHCID 21904668HCID 21904668, compound

Product 1

HCID 12937899343929-61-3Yield 53%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the sulfone from stage (i) (4.84 g, 26.3 mmol) in toluene (100 mL) and THF (70 mL) was added to a solution of DIBAL in toluene (1M, 100 mL, 100 mmol) and the mixture was then heated at reflux for 16 h. After cooling to room temperature EtOH (75 mL) was added cautiously followed by water (100 mL) with stirring. 6M HCl was added to the resulting thick suspension and the organic layer was separated. The aqueous layer was extracted with EtOAc (3×150 mL) and the combined organic layers were dried (MgSO4) and evaporated to a beige solid. Purification by column chromatography [SiO2; DCM/MeOH/880 NH3 (97:3:0.25) increasing polarity to (95:5:0.5)] afforded the desired title phenol as a beige solid (1.85 g, 53%); δH (CD3OD, 400 MHz) 3.13 (2H, t), 3.30 (2H, m), 6.41 (1H, d), 6.60 (1H, s), 6.98 (1H, d); MS m/z (ES−) 151 (M−H+).

Workup

  1. temperaturethe mixture was then heated
  2. temperatureat reflux for 16 h
  3. additionwas added cautiously
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with EtOAc (3×150 mL)
  6. dry with materialthe combined organic layers were dried (MgSO4)
  7. customevaporated to a beige solid
  8. customPurification
  9. temperatureby column chromatography [SiO2; DCM/MeOH/880 NH3 (97:3:0.25) increasing polarity to (95:5:0.5)]

Sources & evidence

ORD record
ord-8f2cb82593e04c2bad6e5006ce8f3e74
Source dataset
uspto-grants-2003_08
Patent number
US06610747B2

Reaction notes

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