Water → HCID 53707521, compound

HRID 248145Notes

Reaction equation

HRID 248145 reaction equation
CC([Si](C)(C)[O:6][CH2:7][C:8]1([CH2:15][O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[O:12][N:11]=[C:10]([CH2:13][CH3:14])[CH2:9]1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CCOCC>O1CCCC1.[Cl-].[Na+].O>[CH2:13]([C:10]1[CH2:9][C@@:8]([CH2:15][O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])([CH2:7][OH:6])[O:12][N:11]=1)[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 2724141Tetrabutylammonium FluorideHCID 19764355HCID 19764355, compound

Product 1

HCID 53707521HCID 53707521, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 500 mg of 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-ethyl-5-[(hexadecyloxy)methyl]-4,5-dihydroisoxazole in 10 ml of tetrahydrofuran is added 2.13 ml of 1M tetrabutylammonium fluoride in tetrahydrofuran. After 2 hours the reaction is poured into water, ether and brine. The organic layer is separated, dried and evaporated, to give 300 mg of the desired compound.

Workup

  1. customThe organic layer is separated
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-346bee70944444a58ab17d9680d175f8
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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