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Tin tetrachloride → [2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-methoxy-phenyl)-methanone

HRID 1841315
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HRID 1841315 반응식
[CH:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([CH:15]([CH3:17])[CH3:16])[C:12]=1[O:13][CH3:14])[C:7]([OH:9])=O)([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl.[Br:29][C:30]1[CH:43]=[CH:42][CH:41]=[CH:40][C:31]=1[CH2:32][C:33]1[O:34][C:35]([CH3:39])=[C:36]([CH3:38])[CH:37]=1>CN(C)C=O.C(Cl)Cl>[Br:29][C:30]1[CH:43]=[CH:42][CH:41]=[CH:40][C:31]=1[CH2:32][C:33]1[O:34][C:35]([CH3:39])=[C:36]([CH3:38])[C:37]=1[C:7]([C:6]1[CH:10]=[C:11]([CH:15]([CH3:17])[CH3:16])[C:12]([O:13][CH3:14])=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=1)=[O:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 24287Tin tetrachlorideHCID 65578Oxalyl chlorideHCID 120939412-(2-Bromo-benzyl)4,5-dimethyl-furanHCID 15895030HCID 15895030, 화합물

생성물 1

HCID 12093942[2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-methoxy-phenyl)-methanone수율 49.2%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
촉매
HCID 6344Dichloromethane용매

실험 절차

The title compound was prepared according to the procedure in Example 5, step 2 using 3,5-diisopropyl-p-anisic acid (0.983 g, 4.16 mmol, RN-117439-59-5), oxalyl chloride (0.398 mL, 4.56 mmol), N,N-dimethylformamide (2 drops), tin (IV) chloride (0.535 mL, 4.58 mmol) and 2-(2-bromo-benzyl)4,5-dimethyl-furan (1.10 g, 4.16 mmol) in CH2Cl2. Purification on Biotage KP-Sil eluting with 3% EtOAc/pet. ether gave 0.990 g (49%) of the title compound as a clear oil. 1H NMR (DMSO-d6) δ1.15 (d, 12 H), 1.84 (s, 3 H), 2.18 (s, 3 H), 3.27 (septet, 2 H), 3.73 (s, 3 H), 3.91 (s, 2 H), 7.12-7.16 (m, 2 H), 7.29 (t, 1 H, 7.44 (s, 2 H), 7.50 (d, 1 H).

후처리

  1. customThe title compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with 3% EtOAc/pet. ether

출처 및 근거

ORD 기록
ord-8b47513f080e44909b8432304b829bbb
출처 데이터셋
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06683107B2

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