Hydrochloric Acid → Benzofuran-3-acetonitrile

HRID 652723

반응식

HRID 652723 반응식
[H-].[Na+].C(OP([CH2:11][C:12]#[N:13])(=O)OCC)C.[O:14]1[CH2:18][C:17](=O)[C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]1=2.Cl>O1CCCC1>[C:12]([CH2:11][C:17]1[C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[O:14][CH:18]=1)#[N:13]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 23556CoumaranoneHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

생성물 1

HCID 2769401Benzofuran-3-acetonitrile수율 98%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
70 °C

실험 절차

To a suspension of 2.64 gms (0.11 mole) of oil free sodium hydride in 200 ml of tetrahydrofuran (THF) was added dropwise a solution of 19.47 gms (0.11 mole) of diethylcyanomethylphosphonate in 75 mL of THF. After the H2 evolution had ceased, a solution of 13.4 g (0.1 mole) of 3-(2H)-benzo[b]-furanone in 100 mL of THF was added. The solution was heated at 70° C. for 1.5 hrs, cooled, and poured into 500 mL of 5% HCl, and washed with ether. The ether phase was washed with brine, dried (MgSO4), filtered and concentrated to give 15.4 g of a dark oil. The product was distilled at 96°-100° C./0.075 mm Hg to give 10.85 g of a yellow oil which crystallized upon standing.

후처리

  1. temperaturecooled
  2. washwashed with ether
  3. washThe ether phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-571137ba63914996b5d887f70ec27da4
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04673680

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