Diisopropylethylamine → 6-Methoxy-3,3-dimethyl-5-{[2-(trimethylsilyl)ethoxy]methoxy}indan-1-one

HRID 2252243Notes

Reaction equation

HRID 2252243 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7](=[O:13])[CH2:6][C:5]2([CH3:15])[CH3:14].C(N(C(C)C)CC)(C)C.[CH3:25][Si:26]([CH2:29][CH2:30][O:31][CH2:32]Cl)([CH3:28])[CH3:27]>C(Cl)Cl>[CH3:12][O:11][C:10]1[CH:9]=[C:8]2[C:4]([C:5]([CH3:15])([CH3:14])[CH2:6][C:7]2=[O:13])=[CH:3][C:2]=1[O:1][CH2:32][O:31][CH2:30][CH2:29][Si:26]([CH3:28])([CH3:27])[CH3:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 134808615-Hydroxy-6-methoxy-3,3-dimethyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 691995296-Methoxy-3,3-dimethyl-5-{[2-(trimethylsilyl)ethoxy]methoxy}indan-1-oneYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-hydroxy-6-methoxy-3,3-dimethyl-indan-1-one (40.0 g, 0.194 mol, see preparation in J. Chem. Soc. Perkin Trans. I 1982, p2013-2017) in CH2Cl2 (400 mL) were added diisopropylethylamine (35.5 mL, 0.204 mol) and SEMCl (34.9 mL, 0.198 mol). The reaction mixture was stirred at room temperature for 3 hours and concentrated. The residue was purified by flash chromatography eluted with EtOAc/hexane (2:8) to give 60.5 g (93%) of the desired product as brown oil. MS (DCI/NH3) m/z: 337.1 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 0.00 (s, 9H) 0.96 (t, J=8.10 Hz, 2H) 1.39 (s, 6H) 2.56 (s, 2H) 3.83 (t, J=8.10 Hz, 2H) 3.90 (s, 3H) 5.39 (s, 2H) 7.15 (s, 1H) 7.20 (s, 1H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography
  3. washeluted with EtOAc/hexane (2:8)

Sources & evidence

ORD record
ord-244cfb7cf3ba41f486ee7fda1d50ab34
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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