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

HRID 1855029
ノート
印刷プレビュー

反応式

HRID 1855029 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran
溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-187411419f274444b0cc31203980c3d5
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08962660B2

反応ノート

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