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

HRID 78869

Reaction equation

HRID 78869 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5f24251b3305495a8d00b73ac4eea0fc
Source dataset
uspto-grants-2014_09
Patent number
US08841477B2

Linked notes

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