Sodium Nitrate → 2-(2-Hydroxy-3,3,3-trifluoropropyl)-6-nitro-3,4-dihydro-2H-1-benzopyran

HRID 582603Notes

Reaction equation

HRID 582603 reaction equation
[OH:1][CH:2]([C:14]([F:17])([F:16])[F:15])[CH2:3][CH:4]1[CH2:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[O:5]1.[N+:18]([O-])([O-:20])=[O:19].[Na+]>FC(F)(F)C(O)=O>[OH:1][CH:2]([C:14]([F:17])([F:15])[F:16])[CH2:3][CH:4]1[CH2:9][CH2:8][C:7]2[CH:10]=[C:11]([N+:18]([O-:20])=[O:19])[CH:12]=[CH:13][C:6]=2[O:5]1

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 153456652-(2-Hydroxy-3,3,3-trifluoropropyl)-3,4-dihydro-2H-1-benzopyran

Product 1

HCID 153456662-(2-Hydroxy-3,3,3-trifluoropropyl)-6-nitro-3,4-dihydro-2H-1-benzopyran

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 8.5 g (35 mmol) of 2-(2-hydroxy-3,3,3-trifluoropropyl)-3,4-dihydro-2H-1-benzopyran in 106 ml of trifluoroacetic acid is treated with 7.4 g (88 mmol) of sodium nitrate at -10° C. The mixture is allowed to react for 45 min, then poured into ice water and the product is extracted with dichloromethane. The organic phase is then dried over sodium sulfate and concentrated under reduced pressure. By chromatography of the residue on a silica column using dichloromethane, 5.0 g of product are obtained.

Workup

  1. customto react for 45 min
  2. extractionthe product is extracted with dichloromethane
  3. dry with materialThe organic phase is then dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customare obtained

Sources & evidence

ORD record
ord-1f3f41036ebe421ebadfd6a2e799cb33
Source dataset
uspto-grants-1999_07
Patent number
US05925662

Reaction notes

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