Sodium hydride → tert-Butyl prop-2-ynyl[3-(tetrahydro-2H-pyran-2-yloxy)propyl]carbamate

HRID 1247582Notes

Reaction equation

HRID 1247582 reaction equation
[CH2:1]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[C:2]#[CH:3].[H-].[Na+].[H][H].Br[CH2:17][CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1>CN(C)C=O.O>[CH2:1]([N:4]([CH2:17][CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])[C:2]#[CH:3]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 86595925tert-Butyl prop-2-ynyl[3-(tetrahydro-2H-pyran-2-yloxy)propyl]carbamateYield 88.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl prop-2-ynylcarbamate (1.2 g) in anhydrous N,N-dimethylformamide (5 ml) was treated with 60% sodium hydride (0.245 g) in one portion. After evolution of hydrogen had ceased 2-(3-bromopropoxy)tetrahydro-2H-pyran (1.36 g) was added. The reaction mixture was stirred under nitrogen for 48 hours then diluted with water (50 ml) and extracted into ethyl acetate (3×25 ml). The combined extracts were dried over anhydrous sodium sulphate, filtered and concentrated to afford the sub-titled compound (1.61 g) as a colourless oil.

Workup

  1. additionwas added
  2. extractionextracted into ethyl acetate (3×25 ml)
  3. dry with materialThe combined extracts were dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e6e6fa17b67c4f52b492892f93688b56
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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