Water → HCID 14986505, compound

HRID 981498Notes

Reaction equation

HRID 981498 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 (3x) 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 (3x)
  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-b12d0e13c8fa4f7ca585d0ce7cb26038
Source dataset
uspto-grants-1991_02
Patent number
US04992435

Reaction notes

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