Triethylamine → HCID 59320872, compound

HRID 341165Notes

Reaction equation

HRID 341165 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[O:3]1.C(N(CC)CC)C.[CH3:24][O:25][CH2:26][C:27](Cl)=[O:28]>C1COCC1.CCOC(C)=O>[CH3:24][O:25][CH2:26][C:27]([NH:15][C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1)=[O:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 59320872HCID 59320872, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (1 g, 4.56 mmol) in THF (20 ml) was added triethylamine (0.95 ml, 6.84 mmol) and methoxyacetyl chloride (0.417 ml, 4.56 mmol) dropwise, the resulting mixture was stirred for 2 hours at RT. The reaction mixture was diluted with EtOAc and washed with water then brine, dried (Na2SO4) filtered and concentrated in vacuo to give the product (1.2 g) as an orange oil.

Workup

  1. washwashed with water
  2. dry with materialbrine, dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d01512b4a58644b3901a2729dbc212fa
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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