Tetrabutylammonium Fluoride → [(3-Hydroxyphenyl)(2-phenoxyethoxy)methylene]-5-chloroadamantane

HRID 990612Notes

Reaction equation

HRID 990612 reaction equation
[O:1]([C:9]1[CH:10]=[C:11]([C:15](=[C:26]2[CH:33]3[CH2:34][CH:29]4[CH2:30][C:31]([Cl:36])([CH2:35][CH:27]2[CH2:28]4)[CH2:32]3)[O:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]=[CH:13][CH:14]=1)[Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:1][C:9]1[CH:10]=[C:11]([C:15](=[C:26]2[CH:27]3[CH2:28][CH:29]4[CH2:30][C:31]([Cl:36])([CH2:32][CH:33]2[CH2:34]4)[CH2:35]3)[O:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 23391585[(3-tert-Butyldimethylsiloxyphenyl)(2-phenoxyethoxy)methylene]-5-chloroadamantane

Product 1

HCID 18415644[(3-Hydroxyphenyl)(2-phenoxyethoxy)methylene]-5-chloroadamantane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4.9 parts of alkene (64) in 75 mL of THF was added 5.0 parts of 70% mixture of tetra-n-butylammonium fluoride in 25 mL of THF over a period of 15 minutes. The reaction mixture was stirred for two hours. TLC on silica gel plate showed the formation of new product. The solvent was evaporated under reduced pressure and the oily material was dissolved in 150 mL of ethyl acetate and washed with two times with 200 mL of water. After drying over anhydrous sodium sulfate, the solvent was evaporated and the oily product was purified on silica gel column. TLC on silica gel plate of the fractions were checked and the combined organic solvent was evaporated, yield 2.5 parts. The structure of the product was confirmed on the basis of 1H NMR. The reaction proceeded as follows:

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe oily material was dissolved in 150 mL of ethyl acetate
  3. washwashed with two times with 200 mL of water
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customthe oily product was purified on silica gel column
  7. customthe combined organic solvent was evaporated
  8. customyield 2.5 parts

Sources & evidence

ORD record
ord-b9f3eebaeb8c4e79a0b8a286315d49cc
Source dataset
uspto-grants-2002_10
Patent number
US06461876B1

Reaction notes

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