Hydrochloric Acid → HCID 89601462, compound

HRID 530241Notes

Reaction equation

HRID 530241 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][C:3]1([O:12][Si](C)(C)C)[C:10]#[N:11].Cl>O1CCCC1>[OH:12][C:3]1([C:10]#[N:11])[CH2:4][C:5]([CH3:8])([CH3:9])[CH2:6][CH2:7][C:2]1([CH3:17])[CH3:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131735643HCID 131735643, compound

Product 1

HCID 89601462HCID 89601462, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
44 °C

Procedure

To a mixture of the product of Example 10d (3.8 g, 15.0 mol) in tetrahydrofuran (29 mL) was added 10% hydrochloric acid (75 mL) and the reaction was stirred at 44° C. for 5 hours. The reaction was concentrated under reduced pressure and the residue diluted with diethyl ether. The organic phase was washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless oil (2.22 g, Yield: 82%). 1H NMR (400 MHz, CDCl3) δ 2.21 (s, 1H), 1.87 (d, J=14.4 Hz, 1H), 1.72 (d, J=14.4 Hz, 1H), 1.66-1.60 (m, 1H), 1.42-1.34 (m, 3H), 1.17 (s, 3H), 1.06 (s, 3H), 1.05 (s, 3H), 1.04 (s, 3H) ppm.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additionthe residue diluted with diethyl ether
  3. washThe organic phase was washed with water (20 mL) and brine (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bce6409cf9ea44d9b7892430d5c56c5c
Source dataset
uspto-grants-2016_05
Patent number
US09353063B2

Reaction notes

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