Hydrochloric Acid → HCID 68849835, compound

HRID 2223008Notes

Reaction equation

HRID 2223008 reaction equation
[OH:1][CH:2]([CH2:6][O:7][C:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]#[N:5].[C:27](OC(=O)C)(=[O:29])[CH3:28].N1C=CC=CC=1.Cl>C(OCC)(=O)C>[C:27]([O:1][CH:2]([CH2:6][O:7][C:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:3][C:4]#[N:5])(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 9841025HCID 9841025, compound

Product 1

HCID 68849835HCID 68849835, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To (±)-3-hydroxy-4-trityloxybutane-nitrile (1.03 g, 3.00 mmol) under N2 was added acetic anhydride (1.53 g, 15.00 mmol) and pyridine (0.26 g, 3.30 mmol) and the resultant mixture was stirred overnight at room temperature. After completion of the reaction (TLC) the reaction mixture was diluted with ethyl acetate (25 mL) and treated with 1N HCl (20 mL). The organic layer was separated, washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated and the residue was purified by column chromatography employing EtOAc-hexane (15:85) as eluent to afford the required 3-acetyloxy-4-trityloxybutanenitrile in nearly quantitative yield. IR (KBr) 3466, 3066, 3019, 2925, 2863, 2235, 1741, 1223, 1004 cm−1; 1HNMR (300 MHz, CDCl3) δ 2.09 (s, 3H), 2.76 (d, 2H, J=5.69, 5.79 Hz), 3.92-4.02 (m, 1H), 7.23-7.41 (m, 15H); Mass (EI) 259, 243, 165, 105, 77.

Workup

  1. customAfter completion of the reaction (TLC) the reaction mixture
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6ce1f7269e0b42318ae1283356ff219b
Source dataset
uspto-grants-2008_05
Patent number
US07374926B2

Reaction notes

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