Sodium hydride → 2-(8-Cyclopropylmethoxy-1,4-dioxaspiro[4.5]dec-8-yl)-4-phenylthiazole

HRID 657517Notes

Reaction equation

HRID 657517 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:12]3([OH:22])[CH2:21][CH2:20][C:15]4([O:19][CH2:18][CH2:17][O:16]4)[CH2:14][CH2:13]3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:26][CH:27]1[CH2:29][CH2:28]1.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH:27]1([CH2:26][O:22][C:12]2([C:9]3[S:10][CH:11]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:8]=3)[CH2:13][CH2:14][C:15]3([O:16][CH2:17][CH2:18][O:19]3)[CH2:20][CH2:21]2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 516892Sodium BicarbonateHCID 59442588HCID 59442588, compound

Product 1

HCID 594425102-(8-Cyclopropylmethoxy-1,4-dioxaspiro[4.5]dec-8-yl)-4-phenylthiazoleYield 88.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.0 g of 8-(4-phenylthiazol-2-yl)-1,4-dioxa-spiro[4.5]decan-8-ol were dissolved in 100 ml of anhydrous DMF and treated with 1.1 g of sodium hydride. The mixture was stirred at room temperature for 15 min, then 6.0 g of bromomethylcyclopropane were added. The mixture was stirred at room temperature for 18 h, then poured onto 400 ml of a saturated aqueous sodium hydrogencarbonate solution and extracted three times with 300 ml each of EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. 8.3 g of the title compound were obtained as a pale yellow oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 h
  2. extractionextracted three times with 300 ml each of EA
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b5f3632f963440fc8df765fcd68e8ea2
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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