Water → HCID 12888291, compound

HRID 1935447Notes

Reaction equation

HRID 1935447 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][CH3:12].[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1.CCOC(C)=O>[CH2:11]([S:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][OH:2])[CH3:12]

Participants

6

Reactant 3

HCID 962WaterHCID 10774274HCID 10774274, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12888291HCID 12888291, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl-2-(ethylthio)benzoate (5.0 g, 25.5 mmol) in dry THF (67 mL) was added to a stirred solution of LAH (17.5 mL of a 1.0 M solution in THF) in an additional 50 mL dry THF at 0° C. under Ar. The reaction was allowed to warm to room temperature while stirring overnight. The resulting clear solution was diluted with EtOAc (140 mL). The mixture was poured into water (300 mL) and the resulting precipitate was filtered off. The filtrate was extracted with ether (3×200 mL) and the combined organic extracts were dried over MgSO4, filtered, concentrated in vacuo and dried overnight on a high vacuum line to yield the title compound as a pale yellow oil:

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. extractionThe filtrate was extracted with ether (3×200 mL)
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customdried overnight on a high vacuum line

Sources & evidence

ORD record
ord-4a6de297a47d4a58982e44b04c4316ef
Source dataset
uspto-grants-2002_05
Patent number
US06387911B1

Reaction notes

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