Triethylamine → HCID 57925997, compound

HRID 1013546Notes

Reaction equation

HRID 1013546 reaction equation
[P:1]([O-:6])([O:4]C)[O:2][CH3:3].Br[C:8]1[CH:9]=[C:10](/[CH:14]=[CH:15]/[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:11]=[CH:12][CH:13]=1.C(N(CC)CC)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:4][P:1]([C:12]1[CH:11]=[C:10](/[CH:14]=[CH:15]/[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:9]=[CH:8][CH:13]=1)([O:2][CH3:3])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11196821HCID 11196821, compoundHCID 21884954Dimethylphosphite

Product 1

HCID 57925997HCID 57925997, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

Dimethyl phosphite (0.089 ml, 0.971 mmol), tert-butyl (2E)-3-(3-bromophenyl)acrylate (0.25 g, 0.883 mmol), triethylamine (0.369 ml, 2.65 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.153 g, 0.132 mmol) were combined and allowed to heat for approximately eight hours at 100° C. The reaction was cooled and filtered over celite, washing with ethyl acetate. The filtrate was concentrated under reduced presesure. The residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane, followed by CH2Cl2/MeOH. MS: calc'c 299 (MH+), exp 299 (MH+).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered over celite
  3. washwashing with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced presesure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-44acfcd686f54caf942b895332c7179e
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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