Tetrahydrofuran → HCID 53950865, compound

HRID 439577Notes

Reaction equation

HRID 439577 reaction equation
O1CCCC1.[O:6]([CH2:14][C@H:15]([O:25][CH2:26][O:27][CH3:28])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[CH3:28][O:27][CH2:26][O:25][C@H:15]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[CH2:14][OH:6]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 54567419HCID 54567419, compound

Product 1

HCID 53950865HCID 53950865, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, to a tetrahydrofuran solution of (R)-1-t-butyldimethylsiloxy-2-methoxymethoxy-3-(2-methoxyphenyl)propane (2.2 g) was added a solution of n tetrabutylammoniumfluoride (1 mol/l, 6.46 ml) in tetrahydrofuranand stirred for 2 hours successively. After tetrahydrofuran wasevaporated in vacuo, water was added, extracted with ethyl acetate,and dried over magnesium sulfate. The solvent was evaporated invacuo, the gained crude product was purified by silica gel columnchromatography, and eluted with a mixed solvent of hexane andethyl acetate (1:1, v/v). The fractions containing the desiredproduct were combined and evaporated in vacuo to obtain (R)-2-methoxymethoxy-3-(2-methoxyphenyl)-1-propanol(1.51 g).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate,and
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated invacuo
  5. customwas purified by silica gel columnchromatography
  6. washeluted with a mixed solvent of hexane andethyl acetate (1:1
  7. additionThe fractions containing the desiredproduct
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-6621b6ece03348978c4fb598a9126fd4
Source dataset
uspto-grants-1996_05
Patent number
US05514773

Reaction notes

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