(1R,2R)-2-(4-bromophenoxy)cyclopentan-1-ol → trans-2-(4-Bromophenoxy)cyclopentyl methanesulfonate

HRID 2060833ノート

反応式

HRID 2060833 の反応式
[CH3:1][S:2]([O:5][C@H:6]1[C@H:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[CH2:9]O[CH2:7]1)(=[O:4])=[O:3].Br[C:20]1C=CC(O[C@@H]2CCC[C@H]2O)=CC=1>>[CH3:1][S:2]([O:5][C@@H:6]1[CH2:7][CH2:20][CH2:9][C@H:10]1[O:11][C:12]1[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=1)(=[O:3])=[O:4]

参加物

3

反応物 2

HCID 67195959(1R,2R)-2-(4-bromophenoxy)cyclopentan-1-olHCID 86653046trans-4-(4-Bromophenoxy)tetrahydrofuran-3-yl methanesulfonate

生成物 1

HCID 86653037trans-2-(4-Bromophenoxy)cyclopentyl methanesulfonate

実験手順

The title compound of Step 2 was prepared according to the general procedure for the synthesis of trans-4-(4-bromophenoxy)tetrahydrofuran-3-yl methanesulfonate in Example 2, except that trans-2-(4-bromophenoxy)cyclopentanol was used in place of trans-4-(4-bromophenoxy)tetrahydrofuran-3-ol, and the reaction mixture was quenched by addition of saturated aqueous ammonium chloride solution. The organic layer was then washed with saturated aqueous ammonium chloride solution, washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated in vacuo to provide product as a brown oil. Yield: 3.86 g, 11.5 mmol, 98%. 1H NMR (400 MHz, CDCl3) δ 1.79-2.00 (m, 4H), 2.14-2.26 (m, 2H), 3.03 (s, 3H), 4.78 (m, 1H), 5.07 (m, 1H), 6.82 (d, J=9.0 Hz, 2H), 7.39 (d, J=9.1 Hz, 2H).

後処理

  1. customthe reaction mixture was quenched by addition of saturated aqueous ammonium chloride solution
  2. washThe organic layer was then washed with saturated aqueous ammonium chloride solution
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide product as a brown oil

出典と根拠

ORDレコード
ord-2957bc1a3a114aceb1161e75ceaf43d1
出典データセット
uspto-grants-2012_10
特許番号
US08278457B2

反応ノート

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