Triethylamine → HCID 21107174, compound

HRID 2377389Notes

Reaction equation

HRID 2377389 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[CH2:9][CH2:8][C:7]2([CH3:14])[CH3:13].C(N(CC)CC)C.[CH3:28][Si:29]([CH3:36])([CH3:35])[CH2:30][CH2:31][O:32][CH2:33]Cl>C1C=CC=CC=1.CN(C)C1C=CN=CC=1.O>[CH3:14][C:7]1([CH3:13])[C:6]2[C:11](=[C:2]([O:1][CH2:33][O:32][CH2:31][CH2:30][Si:29]([CH3:36])([CH3:35])[CH3:28])[CH:3]=[C:4]([C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=2)[C:10](=[O:12])[CH2:9][CH2:8]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 21107256HCID 21107256, compound2×

Product 1

HCID 21107174HCID 21107174, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A solution of 8-hydroxy-4,4-dimethyl-6-trimethylsilanylethynyl-3,4-dihydro-2H-naphthalen-1-one (Intermediate 66, 1.67 g, 5.8 mmol) in anhydrous benzene was treated with triethyl amine (1.41 g, 11.6 mmol) and catalytic amount of 4-(dimethylamino)pyridine followed by 2-(trimethylsilyl)ethoxymethyl chloride (1.93 g, 11.6 mmol) and the resulting reaction mixture was refluxed for 3 days. It was cooled to ambient temperature, diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to an oil that was subjected to flash column chromatography over silica gel (230-400 mesh) using 2-6% ethyl acetate in hexane as the eluent to afford the title product as a yellow oil (1.58 g, 66%).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 3 days
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil that

Sources & evidence

ORD record
ord-ead61852f4474eb894571583be1ccfe8
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

Loading…