HCID 59595156, compound → HCID 688895, compound

HRID 2263650Notes

Reaction equation

HRID 2263650 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]([O:25][CH3:26])=[CH:21][CH:20]=1)/C(OC(C)(C)C)=O)=[O:9]>NC(N)=S.C1(C)C=CC=CC=1>[CH3:26][O:25][C:22]1[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

4

Reactant 1

HCID 59595156HCID 59595156, compound

Product 1

HCID 688895HCID 688895, compound

Reagents, catalysts & solvents 2

HCID 2723790ThioureaCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to general procedure using (E)-tert-butyl 2-(2-hydroxyphenylcarbonyl)-3-(4-methoxyphenyl)prop-2-enoate (35.0 mg, 0.10 mmol), thiourea catalyst III (7 mg, 0.01 mmol) in 1.0 mL toluene for 3 d at −25° C. After completion of reaction, 100 mL sample was withdrawn to determine ee of 3-tert-butylcarboxy-(4-methoxyphenyl)chromanone 12 (90% ee). Anhydrous MgBr2.OEt2 (170 mg) was added to the remaining solution and stirred at RT for 48 h. Purification via column chromatography with 10% EtOAc/hexanes afforded 11 mg (49%) as a yellow solid in 78% ee. Analytical data match those reported in the literature.6

Workup

  1. customPrepared
  2. customfor 3 d
  3. customat −25° C
  4. customAfter completion of reaction, 100 mL sample
  5. customwas withdrawn
  6. additionOEt2 (170 mg) was added to the remaining solution
  7. customPurification via column chromatography with 10% EtOAc/hexanes
  8. customafforded 11 mg (49%) as a yellow solid in 78% ee

Sources & evidence

ORD record
ord-20724ef2c9be497fbcb1f70c08cc7f1a
Source dataset
uspto-grants-2010_12
Patent number
US07851640B2

Reaction notes

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