Triethylamine → HCID 59207311, compound

HRID 2242770Notes

Reaction equation

HRID 2242770 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[S:13][C:12]([CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:11][CH:10]=1.[C:23](Cl)(=[O:27])[C:24]([CH3:26])=[CH2:25]>C(Cl)Cl>[Br:8][C:9]1[S:13][C:12]([CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:27])[C:24]([CH3:26])=[CH2:25])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 59207328HCID 59207328, compound

Product 1

HCID 59207311HCID 59207311, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.10 g, 20.8 mmol) is added dropwise to a solution of 6-(5-bromothiophen-2-yl)methoxyhexanol (3.10 g, 10.62 mmol) and methacryloyl chloride (1.20 g, 11.54 mmol) in DCM (30 mL) at −10° C. This mixture is allowed to warm to room temperature and stirred overnight before it is quenched by the addition water (50 mL) The organic layer is separated and the liquid phase is extracted with DCM (2×30 mL). The organic layers is combined, washed with brine (50 mL), dried (Na2SO4) and evaporated under reduced pressure. The product is purified by column chromatography on silica, eluting with petroleum ether (40-60° C.)/ethyl acetate (90:10) to afford the product as a pale yellow oil (3.27 g, 86%). NMR and MS showed the expected signals.

Workup

  1. customis quenched by the addition water (50 mL) The organic layer
  2. customis separated
  3. extractionthe liquid phase is extracted with DCM (2×30 mL)
  4. washwashed with brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe product is purified by column chromatography on silica
  8. washeluting with petroleum ether (40-60° C.)/ethyl acetate (90:10)

Sources & evidence

ORD record
ord-db4847fe29be4bbf9a4b996fd95feb99
Source dataset
uspto-grants-2010_03
Patent number
US07674397B2

Reaction notes

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