Sodium Hydroxide → 3-Tetrahydropyranyloxyoxetane

HRID 1075310ノート

反応式

HRID 1075310 の反応式
C([O:4][CH2:5][CH:6]([O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)[CH2:7]Cl)(=O)C.[OH-].[Na+]>O>[O:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]1[O:9][CH:6]1[CH2:5][O:4][CH2:7]1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 190484163-Chloro-2-tetrahydropyranyloxy-1-propyl acetate

生成物 1

HCID 540831123-Tetrahydropyranyloxyoxetane収率 100.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To 476 g of crude 3-chloro-2-tetrahydropyranyloxy-1-propyl acetate was added 216 g (5.4 moles) of sodium hydroxide in 500 mL of water. The reaction mixture was heated at reflux for 17 hours. The upper organic layer was separated and taken up in 350 mL of methylene chloride. The methylene chloride solution was dried over sodium sulfate and solvent was removed in vacuo to leave 320.9 g of 3-tetrahydropyranyloxyoxetane: 1H NMR (CDCl3) δ1.63 (br. s, 6H, CH2); 3.2-4.4 (m, 2H, --OCH2); 4.47 (br. s, 1H, CH); 4.67 (br. s, 4H, O(CH2)); 5.17 (br, s, 1H, O--CH); IR (CH2Cl2) 2970, 2910 (C--H); 980 cm-1 (oxetane). Extraction of the aqueous layer with ether gave an additional 10.3 g for an overall crude yield of 331.2 g. 3-Tetrahydropyranyloxyoxetane distilled with some decomposition at 48°-65° (0.2 mm).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 17 hours
  3. customThe upper organic layer was separated
  4. dry with materialThe methylene chloride solution was dried over sodium sulfate and solvent
  5. customwas removed in vacuo

出典と根拠

ORDレコード
ord-a2dd1de55f1442fba8ea25b076590d57
出典データセット
uspto-grants-1983_07
特許番号
US04395561

反応ノート

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