Citric Acid → 1-[5-(Tetrahydro-pyran-2-yloxymethyl)-furan-2-yl]-ethanol

HRID 2040044

反応式

HRID 2040044 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[O:13][C:12]([CH:14]=[O:15])=[CH:11][CH:10]=1.[CH3:16][Mg]Cl.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CC(OC)(C)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[O:13][C:12]([CH:14]([OH:15])[CH3:16])=[CH:11][CH:10]=1

参加物

7

反応物 4

HCID 311Citric AcidHCID 962WaterHCID 130977995-(Tetrahydro-pyran-2-yloxymethyl)-furan-2-carbaldehydeHCID 178418332HCID 178418332、化合物

生成物 1

HCID 668201851-[5-(Tetrahydro-pyran-2-yloxymethyl)-furan-2-yl]-ethanol収率 95%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
1 °C

実験手順

Crude 5-(tetrahydro-pyran-2-yloxymethyl)-furan-2-carbaldehyde (171 g) was dissolved in THF (1 L) and cooled to 1° C. Methylmagnesium chloride (3 M in THF, 325 mL, 0.97 mol) was then added while keeping the internal temperature below 5° C. After the addition, the reaction mixture was stirred at rt for 1 h. Water (1 L), TBME (1 L) and 40% aq. citric acid (200 mL) were added, the layers separated and the org. layer washed with water (500 mL) and evaporated to dryness to give 174 g of crude 1-[5-(tetrahydro-pyran-2-yloxymethyl)-furan-2-yl]-ethanol (95% yield). Part of the crude material (96 g, 0.43 mol) was dissolved in CH2Cl2 (1 L) and treated with MnO2 (371 g, 4.26 mol) at rt. The reaction mixture was heated to 45° C. and stirred at this temperature for 24 h. The mixture was then filtered over celite and the filter cake washed with CH2Cl2. The filtrate was evaporated to dryness to give crude 1-[5-(tetrahydro-pyran-2-yloxymethyl)-furan-2-yl]-ethanone (89 g, 93%) as a yellow oil.

後処理

  1. customthe internal temperature below 5° C
  2. additionAfter the addition
  3. customthe layers separated
  4. washlayer washed with water (500 mL)
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-79cffd202044423b9f56460cec505797
出典データセット
uspto-grants-2013_11
特許番号
US08580831B2

関連ノート

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