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

HRID 78869

反応式

HRID 78869 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 534048934'-Acetoxy-3,5-dihydroxystilbene収率 74%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5f24251b3305495a8d00b73ac4eea0fc
出典データセット
uspto-grants-2014_09
特許番号
US08841477B2

関連ノート

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