Ammonium Chloride → HCID 59774911, compound

HRID 2422491Notes

Reaction equation

HRID 2422491 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Li])CCC.[CH:12]1([C:15]([CH:17]2[CH2:19][CH2:18]2)=[O:16])[CH2:14][CH2:13]1.[Cl-].[NH4+]>C1COCC1>[CH:12]1([C:15]([CH:17]2[CH2:19][CH2:18]2)([OH:16])[C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 70721Dicyclopropyl ketoneHCID 178418339Butyllithium

Product 1

HCID 59774911HCID 59774911, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trimethylsilylacetylene (5 mL, 35.4 mmol) in THF (100 mL) cooled at −78° C., a 1.6M n-butyllithium in hexanes (22.1 mL, 35.4 mmol) was added dropwise. The solution was stirred for 30 min before dicyclopropyl ketone (4.06 mL, 35.4 mmol) was added. The temperature was then slowly raised to room temperature and the reaction was stirred overnight. The reaction was then poured into a saturated ammonium chloride solution and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue obtained was used as such for the next step. 1H NMR (400 MHz, acetone-d6): 4.14 (s, 1H), 1.22-1.10 (m, 2H), 0.65-0.55 (m, 2H), 0.50-0.30 (m, 6H), 0.14 (s, 9H).

Workup

  1. additionwas added
  2. extractionthe aqueous layer was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-48d48d802693427e9b738fcccb8491e9
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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