Tetrabutylammonium Fluoride → 1-(2-Hydroxyethyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene

HRID 1588135Notes

Reaction equation

HRID 1588135 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[C:16]([O:17][CH2:18][O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=[C:13]([O:23][CH2:24][O:25][CH3:26])[C:12]=1[O:27][CH3:28])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][CH2:9][CH2:10][C:11]1[C:16]([O:17][CH2:18][O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=[C:13]([O:23][CH2:24][O:25][CH3:26])[C:12]=1[O:27][CH3:28]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 197572472-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethyl tert-butyldimethylsilyl ether

Product 1

HCID 137145691-(2-Hydroxyethyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

15.0 Milligrams of 2-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethyl tert-butyldimethylsilyl ether was dissolved in 2 ml of anhydrous tetrahydrofuran, under argon gas stream conditions, 0.1 ml of tetrahydrofuran solution of 1 mole of tetra-n-butylammonium fluoride was added thereto and stirred for 30 minutes, the reaction of removal of the protecting group was completed quantitatively. The solvent was removed by evaporation under reduced pressure, and the residue obtained was treated on a silica gel thin layer chromatography and purified by developing with 30% ethyl acetate-n-hexane to yield 9.0 mg of 1-(2-hydroxyethyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene.

Workup

  1. additionwas added
  2. customthe reaction of removal of the protecting group
  3. customThe solvent was removed by evaporation under reduced pressure
  4. customthe residue obtained
  5. additionwas treated on a silica gel thin layer chromatography
  6. custompurified

Sources & evidence

ORD record
ord-cfbe83558bc4444ba32710253b9d5b76
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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