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Sodium Hydroxide → (1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate

HRID 1855029
Notes
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Reaction equation

HRID 1855029 reaction equation
CC1C=CC(S([O:11][CH2:12][C:13]2([CH2:33][O:34][S:35]([C:38]3[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=3)(=[O:37])=[O:36])[CH2:18][CH2:17][C:16](O)(C3C=CC=C(OC4C=CC=CC=4)C=3)[CH2:15][CH2:14]2)(=O)=O)=CC=1.[OH-:45].[Na+]>C1COCC1.O>[CH3:44][C:41]1[CH:42]=[CH:43][C:38]([S:35]([O:34][CH2:33][C:13]23[CH2:18][CH2:17][C:16]([C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([O:45][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[CH:14]=4)([CH2:15][CH2:14]2)[O:11][CH2:12]3)(=[O:37])=[O:36])=[CH:39][CH:40]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 90409620(4-Hydroxy-4-(3-phenoxyphenyl)cyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate)

Product 1

HCID 90408232(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonateYield 171.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

A mixture of (4-hydroxy-4-(3-phenoxyphenyl)cyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate) (390 mg, 0.612 mmol) and powdered NaOH (320 mg, 8.00 mmol) in THF (5 mL) was refluxed for 24 h. The reaction was cooled to rt, diluted with water, and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated in vacuo. The crude oil was purified by flash chromatography on SiO2 (0 to 30% EtOAc:hexanes) to afford the title compound (244 mg, 86% yield) as a white solid. LCMS, [M+H]+=465.2. 1H NMR (500 MHz, CDCl3) δ 7.81 (d, J=8.3 Hz, 2H), 7.42-7.36 (m, 2H), 7.37-7.31 (m, 2H), 7.28 (dd, J=9.6, 6.3 Hz, 1H), 7.15-7.08 (m, 3H), 7.03-6.98 (m, 2H), 6.87 (ddd, J=8.1, 2.4, 0.9 Hz, 1H), 3.83 (d, J=1.3 Hz, 2H), 3.77 (s, 2H), 2.49 (s, 3H), 2.09-1.97 (m, 4H), 1.75 (tt, J=9.6, 2.8 Hz, 2H), 1.69-1.60 (m, 2H).

Workup

  1. temperaturewas refluxed for 24 h
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude oil was purified by flash chromatography on SiO2 (0 to 30% EtOAc:hexanes)

Sources & evidence

ORD record
ord-187411419f274444b0cc31203980c3d5
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08962660B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes