Trichloro-2-propen-1-ylsilane → HCID 57681726, compound

HRID 493460

Reaction equation

HRID 493460 reaction equation
[CH2:1]([Si:4]([Cl:7])(Cl)Cl)[CH:2]=[CH2:3].N12CCCN=C1CCCCC2.[CH3:19][O:20][C:21]([CH3:32])([C@H:23]([OH:31])[C@@H:24]([OH:30])[C:25]([O:28][CH3:29])([CH3:27])[CH3:26])[CH3:22]>C(Cl)Cl>[CH2:1]([Si:4]1([Cl:7])[O:30][C@@H:24]([C:25]([O:28][CH3:29])([CH3:26])[CH3:27])[C@H:23]([C:21]([CH3:32])([O:20][CH3:19])[CH3:22])[O:31]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7867Trichloro-2-propen-1-ylsilaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11218000HCID 11218000, compound

Product 1

HCID 57681726HCID 57681726, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Preparation of (4R,5R)-2-allyl-2-chloro-4,5-bis-(1-methoxy-1-methyl-[1,3,2]dioxasilolane: To a cooled (0° C.) solution of allyltrichlorosilane (7.0 mL; 48 mmol) in CH2Cl2 (80 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (15 mL; 102 mmol). A solution of (3R,4R)-2,5-dimethoxy-2,5-dimethyl-hexane-3,4-diol (10.0 g; 48 mmol) in CH2Cl2 (80 mL) was then added and the mixture was allowed to warm to ambient temperature and stirred for 12 hours. The solution was concentrated and the residue was treated with diethylether (100 mL). The mixture was stirred for 1 hour. The mixture was then filtered and the filtrate was concentrated. The residue was distilled under reduced pressure to give 6.6 g (44%) of (4R,5R)-2-allyl-2-chloro-4,5-bis-(1-methoxy-1-methyl-ethyl)-[1,3,2]dioxasilolane as a clear, colorless liquid.

Workup

  1. concentrationThe solution was concentrated
  2. additionthe residue was treated with diethylether (100 mL)
  3. stirringThe mixture was stirred for 1 hour
  4. filtrationThe mixture was then filtered
  5. concentrationthe filtrate was concentrated
  6. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-75b0dd9355294c39a606712ebada1dd7
Source dataset
uspto-grants-2009_05
Patent number
US07534905B2

Linked notes

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