Hydrochloric Acid → 2-Methyl-2-(phenylsulfanyl)propan-1-ol

HRID 2356025Notes

Reaction equation

HRID 2356025 reaction equation
[CH3:1][C:2]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:7])[C:3](OC)=[O:4].CC(C[AlH]CC(C)C)C.Cl>ClCCl.C1(C)C=CC=CC=1>[CH3:7][C:2]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:1])[CH2:3][OH:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 12467092HCID 12467092, compound

Product 1

HCID 125735892-Methyl-2-(phenylsulfanyl)propan-1-ol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A −78° C. solution of Example 103B (860 mg, 4.1 mmol) in dichloromethane (10 mL) was treated with 1.0M DIBAL-H in toluene (11 mL), warmed to room temperature over 4 hours, poured into a mixture of 3M HCl (15 mL) and ice (˜10 g), and extracted with ethyl acetate (100 mL). The combined extracts were washed with 1M HCl (10 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10-30% ethyl acetate/hexanes to provide the desired product. MS (DCI) m/e 183 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. washThe combined extracts were washed with 1M HCl (10 mL) and brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 10-30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9bdd2b01c55b4f7dbae57530f5762487
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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