Bromoacetic Acid → 4-(2-Furyl)-3-oxaoctanoic acid

HRID 5560

反応式

HRID 5560 の反応式
[H-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C@@H:8]([OH:13])[CH2:9][CH2:10][CH2:11][CH3:12].Br[CH2:15][C:16]([OH:18])=[O:17]>C1COCC1>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]([CH2:9][CH2:10][CH2:11][CH3:12])[O:13][CH2:15][C:16]([OH:18])=[O:17]

参加物

5

反応物 3

HCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 54324361(S)-1-(2-Furyl)-1-pentanol

生成物 1

HCID 197960084-(2-Furyl)-3-oxaoctanoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

NaH (16.3 g, 680.9 mmol) and freshly distilled THF (170 mL) Were stirred at room temperature as (S)-1-(2-furyl)-1-pentanol ([α]25D -17.2°, 30.0 g, 46.0 mmol) in THF (170 mL) was added dropwise. After the addition was complete, the mixture was stirred for 15 m before cautiously heating to reflux for 1 h. The mixture was cooled to 0° C. before adding dropwise a solution of bromoacetic acid (27.3 g, 196.5 mmol) in THF (40 mL). The mixture was refluxed 2 days before cooling and carefully pouring into 600 mL ice water. The aqueous was washed with ether and acidified with HCl to pH 4, and extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4, and evaporated to give a quantitative yield of crude product which was used in the next step without further purification.

後処理

  1. additionwas added dropwise
  2. additionAfter the addition
  3. temperaturebefore cautiously heating
  4. temperatureto reflux for 1 h
  5. temperatureThe mixture was refluxed 2 days
  6. temperaturebefore cooling
  7. washThe aqueous was washed with ether
  8. extractionextracted with ether
  9. washThe combined organic extracts were washed with brine
  10. dry with materialdried over MgSO4
  11. customevaporated

出典と根拠

ORDレコード
ord-c6c1fca572fe4e32bea0275f2d8b6a26
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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