Water → HCID 14986498, compound

HRID 1975067Notes

Reaction equation

HRID 1975067 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 1h. The solution was poured into water (100 mL) and extracted into dichloromethane. The dichloromethane solution was washed with water (3x) 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+); 1 1H NMR (CDCl3) w 1.31 (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 (3x)
  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-eb71c3f5148149ea89996ea9ac1c1f27
Source dataset
uspto-grants-1994_02
Patent number
US05284857

Reaction notes

Loading…