Tetrabutylammonium Fluoride → 2-[5-(4-Methoxyphenoxymethyl)-2-oxooxazolidin-3-yl]propanol

HRID 2294342Notes

Reaction equation

HRID 2294342 reaction equation
[Si]([O:8][CH2:9][CH:10]([N:12]1[CH2:16][CH:15]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[O:14][C:13]1=[O:27])[CH3:11])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH:15]2[O:14][C:13](=[O:27])[N:12]([CH:10]([CH3:11])[CH2:9][OH:8])[CH2:16]2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 214747403-(2-t-Butyldimethylsilyloxy-1-methylethyl)-5-(4-methoxyphenoxymethyl)oxazolidin-2-one

Product 1

HCID 214746992-[5-(4-Methoxyphenoxymethyl)-2-oxooxazolidin-3-yl]propanolYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Preparation 5(b) was repeated, except that 1.26 g of 3-(2-t-butyldimethylsilyloxy-1-methylethyl)-5-(4-methoxyphenoxymethyl)oxazolidin-2-one (polar isomer), obtained as described in Preparation 76, 9.6 ml of tetrabutylammonium fluoride (26% w/v in tetrahydrofuran) and 10 ml of anhydrous tetrahydrofuran were used, to give 0.86 g of the title compound, melting at 62° C. to 67° C., from the polar diastereomer.

Workup

  1. customobtained

Sources & evidence

ORD record
ord-ace886b545db402fac2b9cf44544a068
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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