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

HRID 1816375Notes

Reaction equation

HRID 1816375 reaction equation
[OH:1][CH2:2][C:3]1([CH2:9][OH:10])[CH2:8][O:7][CH2:6][O:5][CH2:4]1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][CH:20]=[C:21]([CH2:23]I)[N:22]=2)=[CH:14][CH:13]=1.[H-].[Na+].FC1C=CC(C2OC=C(CO[C@@H]3CCC[C@H](OCC4C=CC=C(C)C=4C(OC)=O)C3)N=2)=CC=1>CN(C=O)C>[F:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[O:19][CH:20]=[C:21]([CH2:23][O:1][CH2:2][C:3]3([CH2:9][OH:10])[CH2:8][O:7][CH2:6][O:5][CH2:4]3)[N:22]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 803731,3-Dioxane-5,5-dimethanolHCID 219802982-(4-Fluorophenyl)-4-(iodomethyl)oxazoleHCID 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+). Methyl 2-{5-[2-(4-fluorophenyl)oxazol-4-ylmethoxymethyl]-1,3-dioxan-5-ylmethoxymethyl}-6-methylbenzoate 29

Sources & evidence

ORD record
ord-cc2e0a98313f4aeda5124c5c55416801
Source dataset
uspto-grants-2005_04
Patent number
US06884812B2

Reaction notes

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