p-Toluenesulfonic acid → HCID 59595152, compound

HRID 2263647Notes

Reaction equation

HRID 2263647 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:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[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>[CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[C@H:18]1[CH2:10][C:8](=[O:9])[C:3]2[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=2)[O:1]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59595153HCID 59595153, compound

Product 1

HCID 59595152HCID 59595152, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 2723790ThioureaCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to general procedure using (E)-tert-butyl 2-(2-hydroxyphenylcarbonyl)-3-(naphthalen-2-yl)prop-2-enoate (77 mg, 0.20 mmol), thiourea catalyst III (14 mg, 0.020 mmol) in 2.0 mL toluene for 38 h at −25° C. and p-toluenesulfonic acid (19 mg, 0.10 mmol) for 10 h. Purification via column chromatography with 10% EtOAc/hexanes afforded 49 mg (89%) of 9 as a white solid in 91% ee. [α]D: +56.3 (EtOH, c=0.5). Analytical data for 9: IR (film) 1690.9, 1607.9, 1464.8, 1304.4, 1226.9 cm−1; 1H NMR (500 MHz, CDCl3) δ 7.99-7.89 (m, 5H), 7.63-7.54 (m, 4H), 7.13-7.09 (m, 2H), 5.68 (dd, J=13.1, 2.4 Hz, 1H), 3.22 (dd, J=16.8, 13.4 Hz, 1H), 3.00 (dd, J=16.8, 2.7 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 192.2, 161.8, 136.5, 136.3, 133.6, 133.4, 129.0, 128.4, 128.0, 127.3, 126.8 (x2), 125.6, 123.9, 121.9, 121.2, 118.4, 79.9, 44.9; LRMS (electrospray): Exact mass calcd. for C19H14O2 [M]+, 274.10. Found [M]+, 273.8.

Workup

  1. customPrepared
  2. customfor 38 h
  3. customat −25° C.
  4. customPurification via column chromatography with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-56e02546b97b4dac921cb4e7922fdbb3
Source dataset
uspto-grants-2010_12
Patent number
US07851640B2

Reaction notes

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