Iodine → 1,3-Dioxolane-2-propionaldehyde

HRID 76253

반응식

HRID 76253 반응식
Br[CH2:2][CH2:3][CH:4]1[O:8][CH2:7][CH2:6][O:5]1.[Mg].II.CN([CH:15]=[O:16])C>C1COCC1>[O:5]1[CH2:6][CH2:7][O:8][CH:4]1[CH2:3][CH2:2][CH:15]=[O:16]

참가 물질

6

반응물 4

HCID 807IodineHCID 6228DimethylformamideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 5462224Magnesium

생성물 1

HCID 36612141,3-Dioxolane-2-propionaldehyde수율 28%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To the solution of 2-(2-bromoethyl)-1,3-dioxolane (10 g, 55.2 mmol) in THF (50 mL) was added magnesium (1.6 g, 66.3 mmol) and trace amount of I2 as initiator. The reaction mixture was stirred at rt for 2 hrs. After cooling to −78° C., the mixture was quenched with dry DMF (1.39 g, 66.3 mmol) and kept at −78° C. for 2 hrs. After dilution with H2O the reaction mixture was extracted with CH2Cl2 (2×), followed by distillation (45-55° C. @ 8 mmHg) to afford 2 g (28%) of the title compound. MS (DCI/NH4+) m/z 131 (M+H)+.

후처리

  1. temperatureAfter cooling to −78° C.
  2. waitkept at −78° C. for 2 hrs
  3. extractionAfter dilution with H2O the reaction mixture was extracted with CH2Cl2 (2×)
  4. distillationfollowed by distillation (45-55° C. @ 8 mmHg)

출처 및 근거

ORD 기록
ord-cb2e95cbfab14f60ac1af2e9fbf5e1e1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835475B2

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