Urea → Benzyl 2-((1-chlorosilolan-1-yl)oxy)acetate

HRID 530139Notes

Reaction equation

HRID 530139 reaction equation
[CH2:1]1[CH2:5][Si:4]([Cl:7])(Cl)[CH2:3][CH2:2]1.NC(N)=O.[C:12]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:15])[CH2:13][OH:14]>C1COCC1>[Cl:7][Si:4]1([O:14][CH2:13][C:12]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:5][CH2:1][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 1176UreaHCID 75474Silacyclopentane, 1,1-dichloro-HCID 561337Benzyl 2-hydroxyacetate

Product 1

HCID 90418649Benzyl 2-((1-chlorosilolan-1-yl)oxy)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of cyclotetramethylenedichlorosilane (0.5 mL; 3.82 mMol) in dry THF (5 mL) was added urea (0.275 g; 4.58 mmol). The mixture was then cooled to 0° C. and benzyl glycolate (0.54 mL; 3.82 mmol) was then added dropwise over a 7 minute span. The mixture was then taken off the ice bath and allowed to stir at room temperature for 1 hour. The biphasic mixture was then concentrated under high vacuum and diluted with chloroform. The aqueous layer was then soaked up with excess Na2SO4 and the mixture was filtered. The filtrate was concentrated to a light yellow crude liquid which was used without further purification.

Workup

  1. concentrationThe biphasic mixture was then concentrated under high vacuum
  2. additiondiluted with chloroform
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated to a light yellow crude liquid which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-2e2b90b4d392470fa201c8d4c458c7f3
Source dataset
uspto-grants-2016_05
Patent number
US09352049B2

Reaction notes

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