Water → HCID 14986505, compound

HRID 257215Notes

Reaction equation

HRID 257215 reaction equation
C([O:4][CH:5]1[CH:10]([NH:11][C:12](=[O:22])[C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[C:9]2[S:23][C:24]([C:26](=[O:28])[CH3:27])=[CH:25][C:8]=2[O:7][C:6]1([CH3:30])[CH3:29])(=O)C.[OH-].[Na+].O.[K+].[Br-]>CO>[C:26]([C:24]1[S:23][C:9]2[CH:10]([NH:11][C:12](=[O:22])[C:13]3[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=3)[CH:5]([OH:4])[C:6]([CH3:30])([CH3:29])[O:7][C:8]=2[CH:25]=1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 253877Potassium BromideHCID 14986504HCID 14986504, compound

Product 1

HCID 14986505HCID 14986505, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Acetoxy-2-acetyl-5,6-dihydro-5,5-dimethyl-7-(4-nitrobenzamido)-7H-thienopyran (0.60 g, 1.39 mmol) was treated with aqueous sodium hydroxide (1N, 1.5 mL, 1.5 mmol) in methanol (10 mL) at rt and stirred for 2 h. The resultant solution was poured into water and extracted with 5% isopropanol in dichloromethane. The organic phase was washed with water (3×) and dried over magnesium sulfate. The solvent was evaporated in vacuo and the resultant solid triturated in diethyl ether to give the product, 0.36 g (66%), as a pale yellow solid: mp 223°-225° C.; IR (KBr) 1647, 1601, 1530 and 1458 cm-1 ; MS: m/z 391 (MH+); 1H NMR (DMSO-d6): δ 1.23 (s, 3H), 1.42 (s, 3H), 2.45 (s, 3H), 3.84 (m, 1H, simplifies to d, J=8.9 Hz with D2O), 5.01 (m, 1H, simplifies to d, J=8.9 Hz, with D2O), 5.86 (d, J=5.9 Hz, 1H, exchanges with D2O), 7.47 (s, 1H), 8.14 (d, J=8.8 Hz, 2H), 8.36 (d, J=8.8 Hz, 2H) and 9.27 (d, 1H, exchanges with D2O).

Workup

  1. extractionextracted with 5% isopropanol in dichloromethane
  2. washThe organic phase was washed with water (3×)
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe resultant solid triturated in diethyl ether
  6. customto give the product, 0.36 g (66%)

Sources & evidence

ORD record
ord-52bec43a752941c0bd02e00ba0a3184b
Source dataset
uspto-grants-1993_11
Patent number
US05260453

Reaction notes

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