Tetrahydrofuran → 1-(2,3-Epoxypropyl)-cyclododecan-1-ol

HRID 41652

反応式

HRID 41652 の反応式
[C:1]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Mg]Br)C=C.[CH2:19]1[CH2:23][O:22][CH2:21]C1>>[O:22]1[CH2:21][CH:23]1[CH2:19][C:1]1([OH:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 13246CyclododecanoneHCID 178455850HCID 178455850、化合物

生成物 1

HCID 593651121-(2,3-Epoxypropyl)-cyclododecan-1-ol

反応条件

温度
0 °C

実験手順

An oven-dried 500-mL three-neck round-bottom flask was charged with cyclododecanone (6.00 g, 32.9 mmol) and 50 mL dry THF. A 100-mL addition funnel with allyl magnesium bromide (1.0 M solution in THF, 36.2 mL, 36.2 mmol) was attached and the flask was cooled in an ice bath for 10 minutes. The Grignard was slowly dripped in over the course of 30 minutes while stirring at 0° C. under nitrogen. After addition, the ice bath was removed and the reaction mixture was stirred for 4 hours at room temperature under nitrogen. Excess Grignard was quenched by slowly adding water to the reaction mixture cooled to 0° C., and the product was extracted three times with diethyl ether. The organic layer was dried over Na2SO4 and solvent was removed under vacuum to obtain the homoallylic alcohol that was used without further purification.

後処理

  1. temperaturethe flask was cooled in an ice bath for 10 minutes
  2. customwas slowly dripped in over the course of 30 minutes
  3. additionAfter addition
  4. customthe ice bath was removed
  5. stirringthe reaction mixture was stirred for 4 hours at room temperature under nitrogen
  6. customExcess Grignard was quenched by slowly adding water to the reaction mixture
  7. temperaturecooled to 0° C.
  8. extractionthe product was extracted three times with diethyl ether
  9. dry with materialThe organic layer was dried over Na2SO4 and solvent
  10. customwas removed under vacuum

出典と根拠

ORDレコード
ord-55210b283a654f80af1805a764f8de53
出典データセット
uspto-grants-2013_09
特許番号
US08530677B2

関連ノート

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