Sodium Iodide → 4'-Acetoxy-3,5-dihydroxystilbene

HRID 2236330

반응식

HRID 2236330 반응식
[C:1]([O:4][C:5]1[CH:26]=[CH:25][C:8]([CH:9]=[CH:10][C:11]2[CH:16]=[C:15]([O:17]COC)[CH:14]=[C:13]([O:21]COC)[CH:12]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Na+].[I-].C[Si](Cl)(C)C>C(Cl)Cl.CC#N>[C:1]([O:4][C:5]1[CH:26]=[CH:25][C:8]([CH:9]=[CH:10][C:11]2[CH:12]=[C:13]([OH:21])[CH:14]=[C:15]([OH:17])[CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 671702434'-Acetoxy-3,5-bis(methoxymethoxy)stilbene

생성물 1

HCID 534048934'-Acetoxy-3,5-dihydroxystilbene수율 74%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 4′-acetoxy-3,5-bis(methoxymethoxy)stilbene (0.358 g, 1 mmol) in dry DCM (50 mL) and dry CH3CN (50 mL) were added NaI (1.8 g, 24 mmol) and freshly distilled TMSCl (1.52 g, 24 mmol). The mixture was stirred under argon for 15 minutes. The solution was diluted with DCM (50 mL) and washed with a fresh aqueous saturated solution of Na2S2O3 (3×40 mL) and saturated NaHCO3, and water. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified by flash column and gave 0.20 g product (72%). Data are: 1H NMR (Aceton-d6, 300 MHz) δ 8.25 (s, 1H), 7.60 (m, 2H), 7.13-7.08 (m, 4H), 6.59 (d, 2H), 6.32 (t, 1H), 2.25 (s, 3H); 13C NMR (Aceton-d6, 75 MHz) δ 169.7, 159.7, 151.4, 140.4, 136.0, 130.0, 128.3, 128.3, 123.0, 106.1, 103.3, 21.1; HRMS (EI+) found 270.0889 M+, calcd 270.0892 for C16H16O4.

후처리

  1. washwashed with a fresh aqueous saturated solution of Na2S2O3 (3×40 mL) and saturated NaHCO3, and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash column

출처 및 근거

ORD 기록
ord-a46b6296997a4613b02ba9d4a46bbcf7
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07714161B2

연결된 노트

불러오는 중…