Tetrabutylammonium Fluoride → HCID 70393767, compound

HRID 1381645Notes

Reaction equation

HRID 1381645 reaction equation
[CH3:1][C:2]1([CH3:36])[O:6][CH:5]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[CH2:12][O:13][CH:14]=[CH:15][CH:16]=2)[CH:4]([CH2:17][O:18][Si](C2C=CC=CC=2)(C2C=CC=CC=2)C(C)(C)C)[O:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][C:2]1([CH3:36])[O:6][CH:5]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[CH2:12][O:13][CH:14]=[CH:15][CH:16]=2)[CH:4]([CH2:17][OH:18])[O:3]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70393647HCID 70393647, compound

Product 1

HCID 70393767HCID 70393767, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,2-dimethyl-4-[3-oxa-4-phenyl butyl]-5-[3,3-diphenyl-3-t-butyl-2-oxa-3-silapropyl]-1,3-dioxacyclopentane [490 mg, 0.97 mmol] prepared in Part F in THF [5 mL] was treated with tetra-n-butylammonium fluoride [1M in THF, 3 mL] at ambient temperature for two hours. The solvent was removed and the resulting residue was diluted with ether, washed with saturated sodium chloride and dried [MgSO4 ]. The crude product was purified by flash column chromatography to give 204 mg of 2,2-dimethyl-4-[3-oxa-4-phenyl butyl]-5-hydroxymethyl-1,3-dioxacyclopentane. NMR [CDCl3 ]: δ7.33 [s, 5H], 4.52 [s, 2H], 4.30-4.00 [m, 2H], 3.60 [t, 4H], 2.18 [t, 1H, --OH], 1.86 [dt, 2H], 1.43 [s, 3H], 1.33 [s, 3H].

Workup

  1. customThe solvent was removed
  2. additionthe resulting residue was diluted with ether
  3. washwashed with saturated sodium chloride
  4. dry with materialdried [MgSO4 ]
  5. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-05b557bcdc8540cf8b7d82ace1c61e18
Source dataset
uspto-grants-1989_02
Patent number
US04803272

Reaction notes

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