HCID 388023, compound → HCID 388024, compound

HRID 566452Notes

Reaction equation

HRID 566452 reaction equation
[C:1]([C:4]1[S:8][C:7]2[C:9](=[O:17])[C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:15](=[O:16])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[S:8][C:7]2[C:9](=[O:17])[C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:15](=[O:16])[C:6]=2[CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 388023HCID 388023, compoundHCID 4311764Sodium borohydride

Product 1

HCID 388024HCID 388024, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 9 (3.0 g, 11.2 mmol) in MeOH (200 mL) was added NaBH4 (1.5 g, 39.7 mmol) and stirring continued for 2 h. After acidification with dilute HCl, the solution was extracted with CHCl3. The organic fraction was washed with water, dried, and condensed. The residue was purified by column chromatography (silica gel, CHCl3) to give 10 as a yellow solid (mp 166-168° C.) in a 93% yield. IR (KBr) 1650, 1680 (C═O), 3200-3600 (OH) cm−1; 1H NMR (DMSO-d6) δ 1.48 (d, J=6.3 Hz, 3H, CH3), 5.02-5.07 (m, 1H, CH), 6.10 (d, J=4.8 Hz, 1H, OH), 7.45 (s, 1, H-3), 7.62 (d, J=5.1 Hz, 1H, H-7), 8.15 (d, J=5.1 Hz, 1H, H-6); 13C NMR (DMSO-d6): δ 25.3 (C-2-CH3), 64.6 (C-2-CH), 120.7 (C-3), 126.1 (C-7), 135.5 (C-6), 163.0 (C-2), 174.0, 174.4 (C-4, C-8); MS m/z 264 (M+); Anal. (C12H8O3S2) C, H.

Workup

  1. extractionAfter acidification with dilute HCl, the solution was extracted with CHCl3
  2. washThe organic fraction was washed with water
  3. customdried
  4. customcondensed
  5. customThe residue was purified by column chromatography (silica gel, CHCl3)

Sources & evidence

ORD record
ord-d309d7b3a8da440fb9baf30b61ffde2d
Source dataset
uspto-grants-2001_01
Patent number
US06174913B1

Reaction notes

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