Sodium hydride → HCID 88050323, compound

HRID 1884331Notes

Reaction equation

HRID 1884331 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[C:16]1([CH3:42])[C:17]([C:22]([O:24][C@@H:25]2[C@@H:29]([CH2:30][O:31][C:32]([C:34]3[C:35]([CH3:40])=[CH:36][CH:37]=[CH:38][CH:39]=3)=[O:33])[O:28][C@H:27](Cl)[CH2:26]2)=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=1>CN(C)C=O>[C:16]1([CH3:42])[C:17]([C:22]([O:24][C@@H:25]2[C@@H:29]([CH2:30][O:31][C:32]([C:34]3[C:35]([CH3:40])=[CH:36][CH:37]=[CH:38][CH:39]=3)=[O:33])[O:28][C@@H:27]([O:1][C:2]3[CH:11]=[C:10]4[C:5]([C:6]([CH3:13])=[CH:7][C:8](=[O:12])[O:9]4)=[CH:4][CH:3]=3)[CH2:26]2)=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 52805674-MethylumbelliferoneHCID 69913967HCID 69913967, compound

Product 1

HCID 88050323HCID 88050323, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Hydroxy-4-methylcoumarin (226 mg, 1.28 mmol) and sodium hydride (64 mg of a 60% dispersion in mineral oil, 1.6 mmol) were stirred at room temperature for 30 minutes in dry dimethylformamide (4 ml). Then the chloride (423 mg, 1.09 mmol) from Example 16 was added and after 24 hours the mixture was processed as in Stage 1 of Example 17 and the product isolated by flash chromatography on silica gel (eluting with 2% acetone in dichloromethane) to afford an oil which crystallized from hot methanol as colourless crystals (305 mg, 53%). 1H nmr indicated them to be a 91:9 mixture of the title compound and its α-anomer.

Workup

  1. customthe product isolated by flash chromatography on silica gel (eluting with 2% acetone in dichloromethane)
  2. customto afford an oil which
  3. customcrystallized from hot methanol as colourless crystals (305 mg, 53%)
  4. additiona 91:9 mixture of the title compound and its α-anomer

Sources & evidence

ORD record
ord-092404364b0d4c70844a07522f17fc36
Source dataset
uspto-grants-2004_07
Patent number
US06764829B2

Reaction notes

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