Diisopropylethylamine → HCID 21877361, compound

HRID 724400Notes

Reaction equation

HRID 724400 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([O:10][CH3:11])[CH:3]=1.CCN(C(C)C)C(C)C.[CH3:21][Si:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25][CH2:26]Cl>C(Cl)Cl>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:29])([CH3:28])[CH3:21])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6123034-Bromo-2-methoxy-5-methylphenolHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 21877361HCID 21877361, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-2-methoxy-5-methyl-phenol (see Chien-Hsun et al., Syn. Lett., 12, 1351–1352 (1997)) was stirred in dry CH2Cl2 (100 mL) at 23° C. DIEA (6.05 mL, 34.6 mmol), and then 2-(trimethylsilyl)ethoxymethyl chloride (5.6 mL, 31.7 mmol) were added. After stirring for 1 h, the solution was washed with H2O, 0.1 N HCl, H2O, saturated NaHCO3, and brine (25 mL each). Organics were dried (Na2SO4) and concentrated in vacuo. Purification by silica gel chromatography (6% ethyl acetate/hexanes) gave 9.06 g (91%) of [2-(4-bromo-2-methoxy-5-methyl-phenoxymethoxy)-ethyl]-trimethyl-silane as a clear oil. 1H NMR (300 MHz, CDCl3) δ 7.06 (s, 1 H), 7.02 (s, 1 H), 5.24 (s, 2 H), 3.84 (s, 3 H), 3.79 (t, 2 H, J=8.4 Hz), 2.31 (s, 3 H), 0.96 (t, 2 H, J=8.4 Hz), 0.01 (s, 9 H).

Workup

  1. washthe solution was washed with H2O, 0.1 N HCl, H2O, saturated NaHCO3, and brine (25 mL each)
  2. dry with materialOrganics were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by silica gel chromatography (6% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-05ee93bd29de4e50a2299310a199d17e
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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