2-(Dimethylamino)ethanol → F2158-1258

HRID 2243588Notes

Reaction equation

HRID 2243588 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.CC1(C)C(C)(C)[O:36][B:35]([C:40]2[CH:45]=[CH:44][C:43]([OH:46])=[CH:42][CH:41]=2)[O:34]1.[CH3:48][N:49]([CH3:53])[CH2:50][CH2:51]O>C(Cl)Cl>[CH3:48][N:49]([CH2:50][CH2:51][O:46][C:43]1[CH:42]=[CH:41][C:40]([B:35]([OH:34])[OH:36])=[CH:45][CH:44]=1)[CH3:53]

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 11367792F2158-1258

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of solid-supported triphenylphosphine (30.0 g, 30.0 mmol) in DCM (150 mL) was added DEAD (3.93 mL, 25.0 mmol) dropwise via a syringe at room temperature. The reaction mixture was stirred for 1 hr, and then a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenol (4.40 g, 20.0 mmol) and 2-(dimethylamino) ethanol (2.01 mL, 20.0 mmol) in DCM (30 mL) was introduced. The reaction mixture was stirred at room temperature for 2 days. The mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography (eluting with 95:5, DCM/MeOH) to afford 4-dimethylaminoethoxyphenyl boronic acid, pinacol ester (2.25 g) as an yellow oil. MS (MH+) 292.4; Calculated 29 for C16H26BNO3

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 days
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography (eluting with 95:5, DCM/MeOH)

Sources & evidence

ORD record
ord-3198428d88b94a9ea78b698114ab5152
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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