Isopropanol → HCID 388023, compound

HRID 1250216Notes

Reaction equation

HRID 1250216 reaction equation
C([O:4][C:5]1[C:16]2[S:17][CH:18]=[CH:19][C:15]=2[CH:14]=[C:7]2[S:8][C:9]([C:11](=[O:13])[CH3:12])=[CH:10][C:6]=12)(=O)C.CC([OH:23])C.C(Cl)(Cl)Cl>CC(O)=O>[C:11]([C:9]1[S:8][C:7]2[C:14](=[O:23])[C:15]3[CH:19]=[CH:18][S:17][C:16]=3[C:5](=[O:4])[C:6]=2[CH:10]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6212ChloroformHCID 10493719HCID 10493719, compound

Product 1

HCID 388023HCID 388023, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of crude 8 (7.5 g) in HOAc (30 mL) was added CrO3 (5.7 g, 57 mmol). After stirring for 1 h, i-PrOH (20 mL) and CHCl3 (300 mL) were added and stirred for 30 min. The resulting solution was poured into ice water, and the aqueous layer was extracted with CHCl3 three times. The combined extracts were dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, CHCl3) to give 9 (mp 223-225 ° C.) in a 45% yield. IR (KBr) 1650, 1670 (C═O) cm−1; 1H NMR (CDCl3) δ 2.67 (s, 3H, CH3), 7.68 (d, J=5.1 Hz, 1H, H-7), 7.74 (d, J=5.1 Hz, 1H, H-6), 8.12 (s, 1H, H-3); 13C NMR (CDCl3): δ 26.9 (C-2-CH3), 126.9 (C-7), 129.4 (C-3), 134.3 (C-6), 170.0 (C-4), 174.4 (C-8), 190.7 (C-2-C═O); MS m/z 262 (M+); Anal. (C12H6O3S2) C, H.

Workup

  1. stirringstirred for 30 min
  2. extractionthe aqueous layer was extracted with CHCl3 three times
  3. dry with materialThe combined extracts were dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel, CHCl3)

Sources & evidence

ORD record
ord-022fded9eb5d4f9bb099e648a0a4f2cd
Source dataset
uspto-grants-2002_01
Patent number
US06337346B1

Reaction notes

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