Benzene → Ethylene glycol 2,4,6,8-tetramethylcyclotetrasiloxanyl ether 5-norbornene-2-carboxylate

HRID 1356934Notes

Reaction equation

HRID 1356934 reaction equation
[CH3:1][SiH:2]1[O:9][SiH:8]([CH3:10])[O:7][SiH:6]([CH3:11])[O:5][SiH:4]([CH3:12])[O:3]1.[OH:13][CH2:14][CH2:15][O:16][C:17]([CH:19]1[CH2:24][CH:23]2[CH2:25][CH:20]1[CH:21]=[CH:22]2)=[O:18].C1C=CC=CC=1>[Zn](OC(C)=O)OC(C)=O.O>[CH:20]12[CH2:25][CH:23]([CH:22]=[CH:21]1)[CH2:24][CH:19]2[C:17]([O:16][CH2:15][CH2:14][O:13][Si:8]1([CH3:10])[O:9][SiH:2]([CH3:1])[O:3][SiH:4]([CH3:12])[O:5][SiH:6]([CH3:11])[O:7]1)=[O:18]

Participants

6

Reactant 3

HCID 241BenzeneHCID 754041,3,5,7-TetramethylcyclotetrasiloxaneHCID 120338232-Hydroxyethyl bicyclo[2.2.1]hept-5-ene-2-carboxylate

Product 1

HCID 131723964Ethylene glycol 2,4,6,8-tetramethylcyclotetrasiloxanyl ether 5-norbornene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 178476751HCID 178476751, compoundCatalystHCID 962WaterSolvent

Procedure

To a solution containing 1M of 2,4,6,8-tetramethylcyclotetrasiloxane and 0.01 g of (CH3CO2)2Zn was slowly added 1M of 2-hydroxyethyl-5-norbornene-2-carboxylate. The resulting mixture was stirred for 24 hours at a room temperature. Thereafter, 200 mL of benzene and 200 mL of cold water were added. The organic layer was separated, washed with 200 mL of cold water, dried over MgSO4, filtered and concentrated by distillation to provide the title compound of Formula 1A (yield: 97%).

Workup

  1. customThe organic layer was separated
  2. washwashed with 200 mL of cold water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by distillation

Sources & evidence

ORD record
ord-8f82b598863b4a65962c87ac9d6dd82e
Source dataset
uspto-grants-2003_07
Patent number
US06589707B2

Reaction notes

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