Water → HCID 86744625, compound

HRID 982116Notes

Reaction equation

HRID 982116 reaction equation
[N-:1]=[N+:2]=[N-:3].[Li+].Br[CH2:6][C@H:7]1[C:12]2[C:13]([CH3:19])=[CH:14][CH:15]=[C:16]([O:17][CH3:18])[C:11]=2[CH2:10][C@@H:9]([CH2:20][OH:21])[O:8]1.C(OCC)C.O>CN(C=O)C>[N:1]([CH2:6][C@H:7]1[C:12]2[C:13]([CH3:19])=[CH:14][CH:15]=[C:16]([O:17][CH3:18])[C:11]=2[CH2:10][C@@H:9]([CH2:20][OH:21])[O:8]1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 88163Lithium azideHCID 67931201HCID 67931201, compound

Product 1

HCID 86744625HCID 86744625, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Lithium azide (1.0 g, 20 mmol) is added to a solution of [1R,3S] 1-bromomethyl-3,4-dihydro-3-hydroxymethyl-5-methoxy-8-methyl-1H-2-benzopyran (1.77 g, 5.87 mmol), from Step 3, in 20 mL of DMF. The reaction mixture is heated to 70° C. for 1.5 h then cooled to ambient temperature and poured into 50 mL of diethyl ether and 50 mL of water. The layers are separated and the aqueous layer is extracted with 2×50 mL of diethyl ether. The combined ether layers are washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by column chromatography on silica gel to give the title compound.

Workup

  1. temperaturethen cooled to ambient temperature
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with 2×50 mL of diethyl ether
  4. washThe combined ether layers are washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d780531b5e8b492ebc268da293aeedcc
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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