Tetrahydrofuran → Benzenemethanol, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-

HRID 703764ノート

反応式

HRID 703764 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:18][C:19]1[CH:28]=[CH:27][C:22]([C:23](OC)=[O:24])=[CH:21][CH:20]=1>O>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:23][OH:24])=[CH:27][CH:28]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 11770459Benzoic acid, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-, methyl esterHCID 21226445Aluminium lithium hydride

生成物 1

HCID 11413119Benzenemethanol, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-収率 71.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mechanically stirred slurry of 10 g of lithium aluminum hydride and 100 mL of tetrahydrofuran was added dropwise with cooling in an ice bath a solution of 32.9 g (0.139 mol) of methyl 4-tetrahydropyranyloxybenzoate at a rate such that the temperature did not exceed 30° C. After stirring 18 hr at room temperature, the solution was treated cautiously with 100 mL of water. The mixture was filtered, and the filtrate was stirred with 200 mL of aqueous sodium hydroxide for 2 hr. The organic layer was separated and evaporated with a rotary evaporator. The residue was dissolved in 200 mL of ether and washed three times with 5% aqueous sodium bicarbonate and dried over sodium sulfate. Evaporation gave 20.58 g of 4-tetrahydropyranyloxybenzyl alcohol as a liquid. 1H NMR (360 MHz, THF-d8): 1.45-2.0 (m's, 6H, CH2), 3.5 (m, 1H, OCH2), 3.8 (m, 1H, OCH2 ), 4.25 (t, J=6, 1H, OH), 4.45 (d, J=6, 2H, ArCH2OH), 5.35 (t, J=3, 1H, OCHO), 6.95 (d, J=8, 2H, ArH), 7.19 (d, J=8, 2H, ArH).

後処理

  1. customdid not exceed 30° C
  2. filtrationThe mixture was filtered
  3. stirringthe filtrate was stirred with 200 mL of aqueous sodium hydroxide for 2 hr
  4. customThe organic layer was separated
  5. customevaporated with a rotary evaporator
  6. dissolutionThe residue was dissolved in 200 mL of ether
  7. washwashed three times with 5% aqueous sodium bicarbonate
  8. dry with materialdried over sodium sulfate
  9. customEvaporation

出典と根拠

ORDレコード
ord-1cd247bc799f4b4e90caaafe015c3a27
出典データセット
uspto-grants-1991_01
特許番号
US04985332

反応ノート

読み込み中…