Sodium hydride → HCID 86727104, compound

HRID 2175918Notes

Reaction equation

HRID 2175918 reaction equation
[H-].[Na+].[C:3]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].I[CH2:17][CH2:18][C:19]#[CH:20]>CN(C=O)C.CCOCC>[CH2:20]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:19][C:18]#[CH:17]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 96345tert-Butyl ethyl malonateHCID 110844721-Butyne, 4-iodo-

Product 1

HCID 86727104HCID 86727104, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of NaH (60%, 8.50 g, 213 mmol) in 200 mL of DMF was added tert-butyl ethyl malonate (36.3 g, 193 mmol) drop-wise at 25° C. The mixture was stirred for 1 hour and 4-iodobut-1-yne (38.2 g, 212.2 g) was added drop-wise. The resulting suspension was stirred overnight and diluted with 1 L of ether, and washed with water (3×200 mL), brine, dried over anhydrous Na2SO4 and concentrated to afford tert-butyl ethyl but-3-yn-1-ylpropanedioate, which was used directly in the next step.

Workup

  1. stirringThe resulting suspension was stirred overnight
  2. washwashed with water (3×200 mL), brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-806262b988d54a2db9c8b0b03d2352e7
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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