7-Chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carbaldehyde → 1-(6-Chloro-2,3-dihydrobenzo[b][1,4]dioxin-8-yl)ethanol

HRID 2426035노트

반응식

HRID 2426035 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[O:13])[C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.[CH3:14][Mg+].[Br-]>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([OH:13])[CH3:14])[C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1

참가 물질

4

반응물 2

HCID 179446747-Chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carbaldehydeHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 587072601-(6-Chloro-2,3-dihydrobenzo[b][1,4]dioxin-8-yl)ethanol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
0 °C

실험 절차

7-Chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carbaldehyde (0.26 g, 1.32 mmol) was dissolved in 10 mL of diethyl ether and cooled to 0° C. MeMgBr (1.1 mL, 3.31 mmol) was added to the solution and the ice bath was removed. The reaction was allowed to stir at rt for 10 min. and at reflux for 30 min. The reaction was cooled to 0° C. and 10 mL of sat NH4Cl were added to quench the reaction. The diethyl ether layer was separated and washed with water (20 mL×2). The organic layer was dried over Na2SO4 and the solvent was removed by rotary evaporation to collect the desired product (258 mg, 91%). 1H NMR (400 MHz, CDCl3): δ 6.91 (s, 1H), 6.77 (s, 1H), 5.02 (m, 1H), 4.24 (m, 4H), 1.45 (d, 3H).

후처리

  1. customthe ice bath was removed
  2. temperatureat reflux for 30 min
  3. temperatureThe reaction was cooled to 0° C.
  4. addition10 mL of sat NH4Cl were added
  5. customto quench
  6. customthe reaction
  7. customThe diethyl ether layer was separated
  8. washwashed with water (20 mL×2)
  9. dry with materialThe organic layer was dried over Na2SO4
  10. customthe solvent was removed by rotary evaporation
  11. customto collect the desired product (258 mg, 91%)

출처 및 근거

ORD 기록
ord-37f4f94c15b546b88680f69f8c4fc150
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968538B2

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