Sodium hydride → HCID 54232927, compound

HRID 905066Notes

Reaction equation

HRID 905066 reaction equation
[C:1]1([CH:7]([OH:14])[CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:17][C:18]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:19]=1[CH2:20][O:21][C@H:22]1[O:27][C@@H:26]([CH2:28]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:25][CH2:24][CH2:23]1>CN(C)C=O>[Cl:17][C:18]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:19]=1[CH2:20][O:21][C@H:22]1[O:27][C@@H:26]([CH2:28][O:14][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 322392-(1H-imidazol-1-yl)-1-phenylethanolHCID 53994231HCID 53994231, compound

Product 1

HCID 54232927HCID 54232927, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
85 °C

Procedure

1 ml of a dimethylformamide solution containing 23 mg of 1-phenyl-2-(1-imidazolyl)ethanol was heated at 50° C. for 30 minutes with 5 mg of 55% sodium hydride, and then 1 ml of a dimethylformamide solution containing 65 mg of cis-6-(2,4-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran, prepared as described in Example 2(a), were added thereto. The mixture was heated at 85° C. for 3 hours and then the mixture was treated and the product purified essentially as described in (a) above, to give 20 mg of the title compound as a liquid.

Workup

  1. customprepared
  2. additionwere added
  3. additionthe mixture was treated
  4. customthe product purified essentially

Sources & evidence

ORD record
ord-51a9421410af45d789c30a55203db04b
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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