Tetrabutylammonium Fluoride Trihydrate → 3-Hydroxy-9H-xanthen-9-ylideneadamantane

HRID 725703Notes

Reaction equation

HRID 725703 reaction equation
[Si]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13](=[C:23]3[CH:30]4[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:32][CH:24]3[CH2:25]5)[CH2:29]4)[C:14]3[C:19]([O:20][C:21]=2[CH:22]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O.O.O>C1COCC1.CCOCC>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13](=[C:23]3[CH:30]4[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:32][CH:24]3[CH2:25]5)[CH2:29]4)[C:14]3[C:19]([O:20][C:21]=2[CH:22]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

5

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 14645572HCID 14645572, compound

Product 1

HCID 146455733-Hydroxy-9H-xanthen-9-ylideneadamantaneYield 57.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The silylated alkene 5b (1.18 g, 2.6 mmol) was dissolved in 10 ml of THF. n-Bu4NF.3H2O (0.94 g, 3.0 mmol) was added and the yellow solution stirred for 30 min. The solution was then diluted with Et2O (100 mL), washed with H2O (200 mL), and the organic layer was concentrated. Recrystallization from ethyl acetate gave 0.48 g (1.5 mmol, 57.7%) of 5a as a white solid: 235°-240° C. (dec); 1H NMR (CDCl3) delta 1.873 (2, 10H), 1.992 (s, 2H), 3.472 (s, 1H), 3.529 (s, 1H), 6.70-6.76 (m, 2H), 6.96-7.04 (m, 2H), 7.06-7.14 (m, 2H), 7.21-7.29 (m, 2H); HRMS calc. 330.1621, found 330.1617; MS m/e (tel. intensity) 330 (100), 329 (43), 273 (37), 235 (16), 197 (11), 142 (65). Anal. calcd for C23H22 O2 : C, 83.64; H, 6.67. Found; C, 83.75; H, 6.69. ##STR40##

Workup

  1. washwashed with H2O (200 mL)
  2. concentrationthe organic layer was concentrated
  3. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-6538c98283304bbe9ab895d88da74edd
Source dataset
uspto-grants-1998_01
Patent number
US05707559

Reaction notes

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