Hydrochloric Acid → HCID 131729993, compound

HRID 2064534Notes

Reaction equation

HRID 2064534 reaction equation
[CH2:1]([Si:3]([CH2:19][CH3:20])([CH2:17][CH3:18])[C:4]#[C:5][CH2:6][C@@H:7]([CH3:16])[CH2:8][O:9]C1CCCCO1)[CH3:2].Cl.[OH-].[Na+]>O1CCCC1>[CH3:16][C@H:7]([CH2:6][C:5]#[C:4][Si:3]([CH2:19][CH3:20])([CH2:1][CH3:2])[CH2:17][CH3:18])[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131729992HCID 131729992, compound

Product 1

HCID 131729993HCID 131729993, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of triethyl-[(R)-4-methyl-5-(tetrahydro-2H-pyran-2-yloxy)pent-1-inyl]silane (3.84 g, 13 mmol) in tetrahydrofuran (50 mL) was mixed with 2 N hydrochloric acid (50 mL) and stirred for 6 h at 50° C. The reaction mixture was then adjusted to pH 7 with 2 N sodium hydroxide solution (50 mL), concentrated to low volume in a vacuum, and the aqueous phase obtained extracted with ethyl acetate (3×30 mL). The combined organic phases were dried with sodium sulphate and concentrated slightly to low volume in a vacuum. The raw product (3.33 g) was purified by flash chromatography (200 g, 20×5.7 cm) with ethyl acetate /cyclohexane (1:7).

Workup

  1. concentrationconcentrated to low volume in a vacuum
  2. customthe aqueous phase obtained
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. dry with materialThe combined organic phases were dried with sodium sulphate
  5. concentrationconcentrated slightly to low volume in a vacuum
  6. customThe raw product (3.33 g) was purified by flash chromatography (200 g, 20×5.7 cm) with ethyl acetate /cyclohexane (1:7)

Sources & evidence

ORD record
ord-5dc03f46cce04fc2991c71b63d271bf0
Source dataset
uspto-grants-2012_10
Patent number
US08288430B2

Reaction notes

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