4,4,5,5-Tetramethyl[1,3,2]dioxaborolane → HCID 57764577, compound

HRID 1466340Notes

Reaction equation

HRID 1466340 reaction equation
[C:1]([C:3]1[CH:15]=[CH:14][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[CH:2].[CH3:16][C:17]1([CH3:24])[C:21]([CH3:23])([CH3:22])[O:20][BH:19][O:18]1>C1(C)C=CC=CC=1>[CH3:16][C:17]1([CH3:24])[C:21]([CH3:23])([CH3:22])[O:20][B:19](/[CH:2]=[CH:1]/[C:3]2[CH:15]=[CH:14][C:6]([CH2:7][N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)=[CH:5][CH:4]=2)[O:18]1

Participants

4

Reactant 2

HCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 577646034-[(4-Ethynylphenyl)methyl]morpholine

Product 1

HCID 57764577HCID 57764577, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

An oven-dried round-bottom flask was cooled under N2 (g) and then charged with 4-(4-ethynylbenzyl)morpholine (120 mg, 0.596 mmol), toluene (2.5 mL), and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.43 mL, 2.98 mmol). The mixture was stirred for 15 min while purging the solution with N2 (g). HRuCl(CO)(PPh3)3 (29 mg, 0.030 mmol) was then added and the reaction heated to 50° C. for 18 h. The reaction was quenched with NaHCO3 (sat.) (10 mL), extracted with EtOAc, and the organic layer washed with brine (2×) and then dried over MgSO4. The solvent was removed and the resulting residue purified by column chromatography (silica gel, Hexanes/EtOAc, 2:3 to 1:2) to give a white solid (155 mg, 79%). 1H NMR (400 MHz, CDCl3) δ 7.44 (d, 2H, J=8.0 Hz), 7.38 (d, 1H, J=18.8 Hz), 7.30 (m, 2H), 6.15 (d, 1H, J=18.5 Hz), 3.72 (bs, 4H), 3.49 (bs, 2H), 2.45 (bs, 4H), 1.31 (s, 12H); MS ESI 330.1 [M+H]+, calcd for [C19H28BNO3+H]+ 330.22.

Workup

  1. temperatureAn oven-dried round-bottom flask was cooled under N2 (g)
  2. customwhile purging the solution with N2 (g)
  3. customThe reaction was quenched with NaHCO3 (sat.) (10 mL)
  4. extractionextracted with EtOAc
  5. washthe organic layer washed with brine (2×)
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed
  8. customthe resulting residue purified by column chromatography (silica gel, Hexanes/EtOAc, 2:3 to 1:2)

Sources & evidence

ORD record
ord-cdb76da82dfa4830a3dfcd213ea9e778
Source dataset
uspto-grants-2015_04
Patent number
US08999968B2

Reaction notes

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