Tetrahydrofuran → HCID 86690128、化合物

HRID 520429ノート

反応式

HRID 520429 の反応式
[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C:20]1([C:30](OCC)=[O:31])[C:25]([O:27][CH2:28][CH3:29])=[O:26].C1COCC1>CCOCC>[OH:31][CH2:30][C:20]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][O:19]1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 1252434273690-99-0HCID 16710494Lithium tri-tert-butoxyaluminohydride

生成物 1

HCID 86690128HCID 86690128、化合物

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A 1M solution of lithium tri-tert-butoxyaluminum hydride (8.79 mL, 8.79 mmol) was added dropwise to a cold (0° C.) stirred solution of diethyl tetrahydro-2H-pyran-2,2-dicarboxylate (0.810 g, 3.52 mmol) in an. THF (9 mL). After the addition is complete the mixture was allowed to warm to rt and heated to reflux for 4-5 h. The reaction mixture was cooled, diluted with ether and quenched with 20% NaHSO4 solution with vigorous stirring. The organic layer was separated, washed with brine and dried over MgSO4. The crude isolate was purified by silica gel FCC (5% MeOH in DCM) to afford ethyl 2-(hydroxymethyl)tetrahydro-2H-pyran-2-carboxylate as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.29 (q, J=7.0 Hz, 2H), 3.95-3.87 (m, 2H), 3.71 (dd, J=11.2, 8.2 Hz, 1H), 3.62 (dd, J=11.2, 5.1 Hz, 1H), 2.24-2.16 (m, J=8.0, 5.3 Hz, 1H), 2.14-2.06 (m, 1H), 1.84-1.72 (m, 1H), 1.64-1.50 (m, 4H), 1.37-1.29 (m, 3H).

後処理

  1. additionAfter the addition
  2. temperatureheated
  3. temperatureto reflux for 4-5 h
  4. temperatureThe reaction mixture was cooled
  5. customquenched with 20% NaHSO4 solution with vigorous stirring
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. customThe crude isolate
  10. customwas purified by silica gel FCC (5% MeOH in DCM)

出典と根拠

ORDレコード
ord-63618eed7108464481f640c708e6de7a
出典データセット
uspto-grants-2016_05
特許番号
US09326973B2

反応ノート

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