Acetic Anhydride → 5-Acetoxy-3,4-dihydrobenzofuran-6-carboxaldehyde

HRID 986422ノート

反応式

HRID 986422 の反応式
[OH:1][C:2]1[C:3]([CH:11]=[O:12])=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([O:1][C:2]1[CH2:10][CH:6]2[CH2:7][CH2:8][O:9][C:5]2=[CH:4][C:3]=1[CH:11]=[O:12])(=[O:15])[CH3:14]

参加物

4

反応物 2

HCID 7918Acetic AnhydrideHCID 135644765-Hydroxy-2,3-dihydrobenzofuran-6-carbaldehyde

生成物 1

HCID 867419375-Acetoxy-3,4-dihydrobenzofuran-6-carboxaldehyde収率 74%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of 5-hydroxy-2,3-dihydrobenzofuran-6-carboxaldehyde (5.0 g, 0.030 mol) in pyridine (10 ml) was cooled to an internal temperature of -5° C. Acetic anhydride (3.2 g, 0.03 mol) was added dropwise. The cooling bath was removed and the mixture was allowed to stir under nitrogen for 18 hours. The reaction was quenched into water (50 ml) at which time the product crystallized and was collected by filtration. The product was dissolved in methylene chloride (100 ml) and was washed with water (25 ml), saturated sodium bicarbonate (25 ml) saturated sodium chloride (25 ml), dried (MgSO4) and concentrated to a dark oil which solidified on standing. The product was ground, washed with ethyl ether and dried to afford 5-acetoxy-3,4-dihydrobenzofuran-6-carboxaldehyde (4.6 g, 74%). m.p. 68°-70° C.

後処理

  1. customThe cooling bath was removed
  2. customThe reaction was quenched into water (50 ml) at which time the product
  3. customcrystallized
  4. filtrationwas collected by filtration
  5. dissolutionThe product was dissolved in methylene chloride (100 ml)
  6. washwas washed with water (25 ml), saturated sodium bicarbonate (25 ml) saturated sodium chloride (25 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated to a dark oil which
  9. washwashed with ethyl ether
  10. customdried

出典と根拠

ORDレコード
ord-363cf1528dbb422ea90e31eee2917e9b
出典データセット
uspto-grants-1987_12
特許番号
US04713393

反応ノート

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