Iodine → HCID 23293626, 화합물

HRID 862755노트

반응식

HRID 862755 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].II>C(OCC)C.C1C=CC=CC=1.[Zn]>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[OH:11])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 807IodineHCID 7748Ethyl bromoacetateHCID 15194646-Fluoro-1-indanone

생성물 1

HCID 23293626HCID 23293626, 화합물수율 97%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 22174802Benzene ether용매

실험 절차

A mixture of 6-fluoro-1-indanone (5.0 g, 33.3 mmol), ethyl bromoacetate (8.3 g, 50.0 mmol, Aldrich), activated zinc powder (3.2 g, 50.0 mmol, Mallinckrodt; Org. Synth., Coll. Vol. 6, 290, 1988) and a few crystals of iodine in diethyl ether-benzene (1:1, 100 mL) was heated at reflux under nitrogen for 24 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue in diethyl ether was vigorously stirred with excess dilute ammonium hydroxide, dried and concentrated to give ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate as an amber oil (7.6 g, 97%); NMR (DMSO-d6): d 6.99-7.24 (m, 3H, Ar), 5.38 (s, 1H, OH), 4.00 (q, 2H, CH2CH3), 2.64-2.92 (m, 4H, 2XCH2), 2.45-2.54, 2.05-2.14 (2m's, 2H, CH2CO), 1.08 (t,3H, CH3).

후처리

  1. temperatureat reflux under nitrogen for 24 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customdried
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-43e1f15fe6a143ef945e745c2b4e2794
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05719186

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