Furfural → 1-(Furan-2-yl)pentan-1-ol

HRID 5558

反応式

HRID 5558 の反応式
[CH:1](=[O:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([Mg]Br)[CH2:9][CH2:10][CH3:11].[NH4+].[Cl-]>C1COCC1>[O:6]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:1]([OH:7])[CH2:8][CH2:9][CH2:10][CH3:11]

参加物

5

反応物 3

HCID 7362FurfuralHCID 25517Ammonium ChlorideHCID 178418682HCID 178418682、化合物

生成物 1

HCID 2492851-(Furan-2-yl)pentan-1-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Freshly distilled furfural (233.5 g, 2.43 mol) was dissolved in 200 mL freshly distilled THF and added dropwise to a solution of butylmagnesium bromide (2.0 M in THF, 1460 mL, 2.92 mol) at 0° C. under dry nitrogen. After the addition was complete, the mixture was allowed to warm to room temperature overnight. The reaction was recooled to 0° C. and carefully poured into 2 L of cold sat. NH4Cl. The layers were separated, and the aqueous phase was extracted with ether. The combined organic layers were washed with saturated NaCl, dried over MgSO4, evaporated, and vacuum distilled to give 325.6 g (87%): bp 72°-73° C. (0.6 mmHg); 1H NMR (300 MHz, CDCl3) d 7.38 (1H, dd J=1 Hz), 6.33 (1H, m), 6.22 (1H, dd, J=3 Hz), 4.67 (1H, t, J=6 Hz), 2.9 (3H, m), 1.35 (4H, m), 0.90 (3H, t, J=7 Hz); mass spectrum (FAB): 170 (M+NH4).

後処理

  1. additionAfter the addition
  2. customwas recooled to 0° C.
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with ether
  5. washThe combined organic layers were washed with saturated NaCl
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. distillationvacuum distilled
  9. customto give 325.6 g (87%)

出典と根拠

ORDレコード
ord-6c6d592bcf1a42debe7854b152d5967a
出典データセット
uspto-grants-1993_09
特許番号
US05244910

関連ノート

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