2-Methylbenzenesulfonic acid → HCID 20079663, compound

HRID 1654122Notes

Reaction equation

HRID 1654122 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[O:4][C:5]([CH2:16][C:17]#[CH:18])=[CH:6][C:7]=1[CH2:8][O:9]C1CCCCO1.C1(C)C(S(O)(=O)=O)=CC=CC=1>CO>[F:20][C:2]([F:1])([F:19])[C:3]1[O:4][C:5]([CH2:16][C:17]#[CH:18])=[CH:6][C:7]=1[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 20079651HCID 20079651, compound

Product 1

HCID 20079663HCID 20079663, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

1.1 g of the product of Stage F were mixed in 25 ml of methanol and 50 mg of toluenesulfonic acid were added. The mixture was stirred at 20° C. for 2 hours and poured into ice-cold water and extracted with isopropyl ether. The extract was dried and the solvent was evaporated. The residue was chromatographed on silica (eluent: 7/3 hexane/ethyl acetate) to obtain 600 mg of the expected alcohol.

Workup

  1. additionpoured into ice-cold water
  2. extractionextracted with isopropyl ether
  3. customThe extract was dried
  4. customthe solvent was evaporated
  5. customThe residue was chromatographed on silica (eluent: 7/3 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e9c89a4754da490f9b1fd48bafcf0764
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

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