Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 90418188, compound

HRID 2177339Notes

Reaction equation

HRID 2177339 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([F:13])[S:10][C:9]=2[CH2:14][O:15]C2CCCCO2)=[CH:4][CH:3]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([F:13])[S:10][C:9]=2[CH2:14][OH:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 90418752HCID 90418752, compound

Product 1

HCID 90418188HCID 90418188, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 250-mL round-bottom flask, was placed 2-[[3-(4-chlorophenyl)-5-fluorothiophen-2-yl]methoxy]oxane (1.6 g, 4.90 mmol, 1.00 equiv), ethanol (100 mL), PPTS (120 mg, 0.48 mmol, 0.10 equiv). The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:2). This resulted in 0.7 g (59%) of [3-(4-chlorophenyl)-5-fluorothiophen-2-yl]methanol as yellow oil.

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThis resulted in 0.7 g (59%) of [3-(4-chlorophenyl)-5-fluorothiophen-2-yl]methanol as yellow oil

Sources & evidence

ORD record
ord-9fb7ba8b2f8f43378b34b27a2a5bef95
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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