Furfuryl Alcohol → 6-Acetoxy-2H-pyran-3(6H)-one

HRID 2170522ノート

反応式

HRID 2170522 の反応式
[CH2:1]([OH:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].[C:13]([O-:16])(=[O:15])[CH3:14].[Na+].BrN1C(=O)CCC1=O.C(OC(=O)C)(=O)C>O.C1COCC1>[C:13]([O:16][CH:5]1[CH:4]=[CH:3][C:1](=[O:7])[CH2:2][O:6]1)(=[O:15])[CH3:14]

参加物

8

反応物 5

HCID 7361Furfuryl Alcohol2 回HCID 7918Acetic AnhydrideHCID 67184N-bromobutanimideHCID 516892Sodium Bicarbonate2 回HCID 517045Sodium Acetate

生成物 1

HCID 111162906-Acetoxy-2H-pyran-3(6H)-one収率 42.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

500 g (5.10 mol) of furfuryl alcohol (Compound 1) was dissolved in 1.65 L of water and 6.6 L of THF in a nitrogen gas stream and cooled to 0° C. or lower. To this, a mixture of 855 g (10.2 mol) of sodium hydrogen carbonate, 418 g (5.10 mol) of sodium acetate and 953 g (5.35 mol) of N-bromosuccinimide was added by spending 40 minutes. Thereafter, the resultant was agitated for an hour, and 2,083 g (20.4 mol) of acetic anhydride was added at 0° C. or lower. Then, the resultant was heated to room temperature and agitated overnight. At the end of the reaction, 20.5 L of a saturated aqueous sodium hydrogen carbonate solution was added, followed by extraction with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and subjected to vacuum concentration to obtain 776 g of a crude product (crude yield: 42.6%). The obtained crude product was subjected to column purification (n-Hex:AcOEt=3:1) to obtain 339 g of Compound (±) 4 as a yellow-brown oily product.

後処理

  1. additionwas added
  2. stirringagitated overnight
  3. additionwas added
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. concentrationsubjected to vacuum concentration
  7. customto obtain 776 g of a crude product (crude yield: 42.6%)
  8. customThe obtained crude product
  9. customwas subjected to column purification (n-Hex:AcOEt=3:1)

出典と根拠

ORDレコード
ord-d61f8eebc6cc4320a14f4e5006875623
出典データセット
uspto-grants-2015_06
特許番号
US09051288B2

反応ノート

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