Sodium hydride → 5-(2-(4-Fluorophenyl)oxazol-4-ylmethoxymethyl)-1,3-dioxan-5-ylmethanol

HRID 748012Notes

Reaction equation

HRID 748012 reaction equation
[OH:1][CH2:2][C:3]1([CH2:9][OH:10])[CH2:8][O:7][CH2:6][O:5][CH2:4]1.[I-].[H-].[Na+].[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[O:22][CH:23]=[C:24]([CH2:26]O[C@@H]3CCC[C@H](OCC4C=CC=C(C)C=4C(OC)=O)C3)[N:25]=2)=[CH:17][CH:16]=1>CN(C=O)C>[F:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[O:22][CH:23]=[C:24]([CH2:26][O:1][CH2:2][C:3]3([CH2:9][OH:10])[CH2:8][O:7][CH2:6][O:5][CH2:4]3)[N:25]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 30165Iodide IonHCID 803731,3-Dioxane-5,5-dimethanolHCID 58681954Methyl cis-2-(3-(2-(4-fluorophenyl)oxazol-4-ylmethoxy)cyclohexyloxymethyl)-6-methylbenzoate

Product 1

HCID 224936845-(2-(4-Fluorophenyl)oxazol-4-ylmethoxymethyl)-1,3-dioxan-5-ylmethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g (6.7 mmol) of 5-hydroxymethyl-1,3-dioxan-5-ylmethanol and 0.5 g (16.5 mmol) of 2 were dissolved in 20 ml of dry DMF. 300 mg of 55% NaH in paraffin oil were added, and the mixture was then stirred at room temperature for 1 hour. Work-up was carried out analogously to the synthesis of compound 5b. This gave 28 as a white amorphous solid. TLC (n-heptane/ethyl acetate 1:2). Rf=0.4. C16H18FNO5 (323.33) MS(ESI) 324.2 (M+H+).

Sources & evidence

ORD record
ord-4bfc84fda3bf4495b1171686e9b89ba3
Source dataset
uspto-grants-2008_07
Patent number
US07399777B2

Reaction notes

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