Nitric Acid → 5,6-Dihydro-6-hydroxy-5,5-dimethyl-2-nitro-7-(2-oxopyrrolidin-1-yl)-7H-thieno[3,2-b]pyran

HRID 981493Notes

Reaction equation

HRID 981493 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][CH:6]1[C:11]([CH3:13])([CH3:12])[O:10][C:9]2[CH:14]=[CH:15][S:16][C:8]=2[CH:7]1[N:17]1[CH2:21][CH2:20][CH2:19][C:18]1=[O:22].[K+].[Br-]>C(O)(=O)C>[OH:5][CH:6]1[C:11]([CH3:12])([CH3:13])[O:10][C:9]2[CH:14]=[C:15]([N+:1]([O-:4])=[O:2])[S:16][C:8]=2[CH:7]1[N:17]1[CH2:21][CH2:20][CH2:19][C:18]1=[O:22]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 253877Potassium BromideHCID 99034645,6-Dihydro-6-hydroxy-5,5-dimethyl-7-(2-oxopyrrolidin-1-yl)-7H-thieno[3,2-b]pyran

Product 1

HCID 149864945,6-Dihydro-6-hydroxy-5,5-dimethyl-2-nitro-7-(2-oxopyrrolidin-1-yl)-7H-thieno[3,2-b]pyran

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Nitric acid (90%, 1.2 mL, 26.9 mmol) was added to a solution of 5,6- dihydro-6-hydroxy-5,5-dimethyl-7-(2-oxopyrrolidin-1-yl)-7H-thieno[3,2-b]pyran (1.0 g, 3.74 mmol) in acetic acid (30 mL) at 18° C., and stirred at rt for 1.5 h. The resultant solution was poured into ice water (200 mL). Within 10 min a yellow solid crystallized which was collected by filtration, washed with water and triturated in diethyl ether to give the product, 0.487 g (42%), as a yellow solid: mp 214°-217° C.; IR (KBr): 3216, 1655 and 1512 cm-1 ; MS: m/z 313 (MH+); 1H NMR

Workup

  1. customWithin 10 min a yellow solid crystallized which
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customtriturated in diethyl ether
  5. customto give the product, 0.487 g (42%)

Sources & evidence

ORD record
ord-21e965d7515c4f56a2d072af767e40c4
Source dataset
uspto-grants-1991_02
Patent number
US04992435

Reaction notes

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