Water → HCID 14986498, compound

HRID 1086638Notes

Reaction equation

HRID 1086638 reaction equation
[OH-].[Na+].C([O:6][CH:7]1[C:12]([CH3:14])([CH3:13])[O:11][C:10]2[CH:15]=[C:16]([C:18](=[O:20])[CH3:19])[S:17][C:9]=2[CH:8]1[N:21]1[CH2:25][CH2:24][CH2:23][C:22]1=[O:26])(=O)C.O.[K+].[Br-]>CO>[C:18]([C:16]1[S:17][C:9]2[CH:8]([N:21]3[CH2:25][CH2:24][CH2:23][C:22]3=[O:26])[CH:7]([OH:6])[C:12]([CH3:14])([CH3:13])[O:11][C:10]=2[CH:15]=1)(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 253877Potassium BromideHCID 14986496HCID 14986496, compound

Product 1

HCID 14986498HCID 14986498, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous sodium hydroxide (50%, 0.15 g, 1.87 mmol) was added to a solution of 6-acetoxy-2-acetyl-5,6-dihydro-5,5-dimethyl-7-(2-oxopyrrolidin-1-yl)-7H-thieno[3,2-b]pyran (0.45 g, 1.28 mmol) in methanol (20 mL) and stirred at rt for 1 h. The solution was poured into water (100 mL) and extracted into dichloromethane. The dichloromethane solution was washed with water (3×) and dried over magnesium sulfate. The solvent was evaporated in vacuo and the resultant oil was crystallized from diethyl ether and hexanes to give the product, 0.327 g (83%), as a colorless solid: mp 102°-106° C.; IR (KBr): 1665 and 1561 cm-1 ; MS: m/z 310 (MH+); 1H NMR (CDCl3): δ1.31(s, 3H), 1.51(s, 3H), 2.07(m, 2H), 2.48(s, 3H), 2.51(m, 2H), 3.34(m, 2H), 3.45(d, J=6.2 Hz, 1H, exchanges with D2O), 3.80(dd, J=6.2 Hz and J=9.4 Hz, 1H, simplifies to d, J=9.4 Hz, with D2O), 5.29(d, J=9.4 Hz, 1H) and 7.14(s, 1H).

Workup

  1. extractionextracted into dichloromethane
  2. washThe dichloromethane solution was washed with water (3×)
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe resultant oil was crystallized from diethyl ether and hexanes
  6. customto give the product, 0.327 g (83%)

Sources & evidence

ORD record
ord-37ff3a41407e432ebcc581ab58f84ed1
Source dataset
uspto-grants-1991_07
Patent number
US05030736

Reaction notes

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