Tetrabutylammonium Fluoride → 3-{[(1S)-1-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methyl}-1,3-oxazolidin-2-one

HRID 2056761Notes

Reaction equation

HRID 2056761 reaction equation
[Si]([O:18][CH2:19][CH2:20][C@H:21]1[C:26]2[CH:27]=[CH:28][C:29]([CH2:31][N:32]3[CH2:36][CH2:35][O:34][C:33]3=[O:37])=[CH:30][C:25]=2[CH2:24][CH2:23][O:22]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:18][CH2:19][CH2:20][C@H:21]1[C:26]2[CH:27]=[CH:28][C:29]([CH2:31][N:32]3[CH2:36][CH2:35][O:34][C:33]3=[O:37])=[CH:30][C:25]=2[CH2:24][CH2:23][O:22]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 693083913-{[(1S)-1-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methyl}-1,3-oxazolidin-2-one

Product 1

HCID 693084103-{[(1S)-1-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methyl}-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-{[(1S)-1-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methyl}-1,3-oxazolidin-2-one (0.22 g, 0.43 mmol) in dry THF (30 ml) was added tetrabutylammonium fluoride (1M solution in THF) (0.51 mL, 0.51 mmol) and the reaction stirred at room temperature under nitrogen over the weekend. The reaction was quenched by addition of water and extracted with dichloromethane. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica, eluting with methanol/dichloromethane (1:9), to yield the title compound as a colourless oil.

Workup

  1. customThe reaction was quenched by addition of water
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude product was purified by flash chromatography on silica
  7. washeluting with methanol/dichloromethane (1:9)

Sources & evidence

ORD record
ord-bd734c6dfc71466c8d9a99b936348e37
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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