Water → HCID 23326846, compound

HRID 1380380Notes

Reaction equation

HRID 1380380 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:7]([C:9]([CH3:25])([O:14][N:15]1[C:20]([CH3:22])([CH3:21])[CH2:19][CH2:18][CH2:17][C:16]1([CH3:24])[CH3:23])[CH2:10][CH2:11][CH2:12][OH:13])#[N:8].C(N(CC)CC)C.O>C(OCC)C>[C:1]([O:13][CH2:12][CH2:11][CH2:10][C:9]([C:7]#[N:8])([O:14][N:15]1[C:20]([CH3:22])([CH3:21])[CH2:19][CH2:18][CH2:17][C:16]1([CH3:24])[CH3:23])[CH3:25])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 13528Methacryloyl chlorideHCID 18353566HCID 18353566, compound

Product 1

HCID 23326846HCID 23326846, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Methacryloyl chloride (174 mg, 1.7 mmol) in diethyl ether (5 ml) was slowly added to a cooled (0° C.) solution of 1-(1-cyano-4-hydroxy-1-methylbutoxy)-2,2,6,6-tetramethylpiperidine (Example 6) (150 mg, 0.56 mmol) in diethyl ether (10 ml) containing triethylamine (339 mg, 3.3 mmole). The reaction was stirred at ambient temperature for 1 hr after which was added triethylamine (2 ml) and water (10 ml) and stirred for a further hour. The layers were separated and the ether layer washed with saturated bicarbonate, water, brine, dried over magnesium sulphate and concentrated. Chromatography using silica gel and dichloromethane as eluent gave the title compound as a colourless oil (132 mg, 70% yield). 1H NMR δ (CDCl3): 1.1 (9H, s), 1.3 (4H, s), 1.5 (5H, broad s), 1.95 (7H, m), 4.2 (2H, m, OCH2), 5.5 (1H, m, olefinic CH2), 6.1 (1H, broad s, olefinic CH2). Mass spectrum CI (CH4) m/e: 337 (MH+), 156, 140.

Workup

  1. stirringstirred for a further hour
  2. customThe layers were separated
  3. washthe ether layer washed with saturated bicarbonate, water, brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c46a55f77c64453fbef366b6902714bd
Source dataset
uspto-grants-1986_04
Patent number
US04581429

Reaction notes

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