Diisobutylaluminum hydride → 2-(4,6-Dichloropyrimidin-5-yl)ethan-1-ol

HRID 1192423Notes

Reaction equation

HRID 1192423 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[C:6]([Cl:12])=[N:7][CH:8]=[N:9][C:10]=1[Cl:11].CC(C[AlH]CC(C)C)C>CCOCC>[Cl:11][C:10]1[C:5]([CH2:4][CH2:3][OH:2])=[C:6]([Cl:12])[N:7]=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 54165419Methyl 2-(4,6-dichloropyrimidin-5-yl)acetate

Product 1

HCID 529881462-(4,6-Dichloropyrimidin-5-yl)ethan-1-olYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (4,6-Dichloro-pyrimidin-5-yl)-acetic acid methyl ester (0.52 g, 2.35 mmol) in ether (40 mL) at −78° C. was added DIBAL-H (1.5M, 4 mL, 6.05 mmol) dropwise. After addition, the mixture was allowed to warm up to room temperature and stirred for 3 hours. Then quenched with 2N HCl (10 mL) at −78° C. Extracted with ethyl acetate (3×50 mL). The organic phase was dried and concentrated to give fairly pure 2-(4,6-Dichloro-pyrimidin-5-yl)-ethanol (0.44 g, 97%). 1H NMR (CDCl3, 400 MHz) δ 8.66 (s, 1H), 3.96 (t, J=6.8 Hz, 2H), 3.23 (t, J=6.8 Hz, 2H). 1.65 (s, 1H). MS (APCI+) [M+H]+194.

Workup

  1. additionAfter addition
  2. customThen quenched with 2N HCl (10 mL) at −78° C
  3. extractionExtracted with ethyl acetate (3×50 mL)
  4. customThe organic phase was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cf6481d6f94a47be818632d6a07446c4
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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