Water → HCID 14986498, compound

HRID 981494Notes

Reaction equation

HRID 981494 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+); 1H NMR (CDCl3): δ 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-b1bc2d1ee7ff48feadb986b126cee7e5
Source dataset
uspto-grants-1991_02
Patent number
US04992435

Reaction notes

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