Water → HCID 14986458, compound

HRID 654684Notes

Reaction equation

HRID 654684 reaction equation
[O:1]1CCC[CH2:2]1.[F-].[CH2:7]([N+](CCCC)(CCCC)CCCC)CCC.[Si](OCCO[C:35]1[C:44]2[C:39](=[C:40]([CH3:45])[CH:41]=[CH:42][CH:43]=2)[C:38]([O:46][CH3:47])=[C:37]([O:48][CH3:49])[CH:36]=1)(C(C)(C)C)(C)C.[OH2:50]>>[OH:50][CH2:7][C:35]1[C:44]2[C:39](=[C:40]([CH3:45])[CH:41]=[CH:42][CH:43]=2)[C:38]([O:46][CH2:47][O:1][CH3:2])=[C:37]([O:48][CH3:49])[CH:36]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 67741520HCID 67741520, compound

Product 1

HCID 14986458HCID 14986458, compound

Procedure

32 ml of a tetrahydrofuran solution of 1M tetra-n-butylammonium fluoride was added to a tetrahydrofuran (150 ml) solution of 7.3 g of 1-(t-butyldimethylsilyl)oxymethyl-3-methoxy-4-methoxy-methoxy-5-methylnaphthalene and agitated for 1 hour. Water was added to the reaction solution and extracted with ethyl acetate, and the resultant organic phase was washed with water and a saturated saline solution, followed by drying with anhydrous magnesium sulfate and removal of the solvent by distillation to obtain the captioned compound as an oily substance. This compound was used for subsequent reaction without purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe resultant organic phase was washed with water
  3. dry with materialby drying with anhydrous magnesium sulfate and removal of the solvent by distillation
  4. customto obtain the captioned compound as an oily substance
  5. customThis compound was used for subsequent reaction without purification

Sources & evidence

ORD record
ord-0f42a6eb83b047f3b042229b63394ba2
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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