p-Toluenesulfonic acid → HCID 6923206, compound

HRID 2263649Notes

Reaction equation

HRID 2263649 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[C:9](\[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25])=[O:18])/C(OC(C)(C)C)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>NC(N)=S.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[CH2:9][C:17](=[O:18])[C:19]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:25]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59595150HCID 59595150, compound

Product 1

HCID 6923206HCID 6923206, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 2723790ThioureaCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to general procedure using (E)-tert-butyl 3-(2-chlorophenyl)-2-(2-hydroxyphenylcarbonyl)prop-2-enoate (36 mg, 0.10 mmol), thiourea catalyst III (7 mg, 0.010 mmol) in 1.0 mL toluene for 36 h at −25° C. and p-toluenesulfonic acid (10 mg, 0.05 mmol) for 50 h. Purification via column chromatography with 10% EtOAc/hexanes afforded 19 mg (67%) of 11 as a white solid in 88% ee. Analytical data match those reported in the literature.6

Workup

  1. customPrepared
  2. customfor 36 h
  3. customat −25° C.
  4. customPurification via column chromatography with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-61e53c1fa6b04ffc99be5f6547f1dc8c
Source dataset
uspto-grants-2010_12
Patent number
US07851640B2

Reaction notes

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