p-Toluenesulfonic acid → HCID 726870, compound

HRID 2263648Notes

Reaction equation

HRID 2263648 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](/[C:10](=[CH:18]\[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)/C(OC(C)(C)C)=O)=[O:9].C1(C)C=CC(S(O)(=O)=O)=CC=1>NC(N)=S.C1(C)C=CC=CC=1>[C:22]1([CH3:25])[CH:23]=[CH:24][C:19]([C@H:18]2[CH2:10][C:8](=[O:9])[C:3]3[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=3)[O:1]2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59595154HCID 59595154, compound

Product 1

HCID 726870HCID 726870, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 2723790ThioureaCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to general procedure using (E)-tert-butyl 2-(2-hydroxyphenylcarbonyl)-3-p-tolylprop-2-enoate (54 mg, 0.16 mmol), thiourea catalyst III (11 mg, 0.016 mmol) in 1.6 mL toluene for 36 h at −25° C. and p-toluenesulfonic acid (15 mg, 0.08 mmol) for 25 h. Purification via column chromatography with 10% EtOAc/hexanes afforded 32 mg (83%) of 10 as a white solid in 90% 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-de2d6ecd3eb241b49fb7ba90f03edb5a
Source dataset
uspto-grants-2010_12
Patent number
US07851640B2

Reaction notes

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