Chlorotrimethylsilane → 3,4-Bis-trimethylsilanyloxy-tetrahydro-furan

HRID 1046449Notes

Reaction equation

HRID 1046449 reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].[CH2:6]1[O:12][CH2:11][C@@H:9]([OH:10])[C@H:7]1[OH:8].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][Si:2]([CH3:4])([CH3:3])[O:8][CH:7]1[CH:9]([O:10][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH2:11][O:12][CH2:6]1

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 6417731,4-Anhydroerythritol

Product 1

HCID 668503653,4-Bis-trimethylsilanyloxy-tetrahydro-furanYield 107.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

TMSCl (8.0 mL, 63.32 mmol) was added dropwise to a solution of 1,4-anhydroerythritol (3.0 g, 28.81 mmol), triethylamine (9.2 mL, 66.0 mmol) and DMAP (few crystals) in dichloromethane (200 mL) at 0° C. The reaction was allowed to slowly warm to room temperature over 1 h and then stirred for an additional 3 h. The solid was filtered and the filtrate concentrated to give a solid. The solid was then filtered through a short silica gel column eluting with 33% hexanes in ethyl ether. Removal of solvents under reduced pressure provided 3,4-bis-trimethylsilanyloxy-tetrahydro-furan (7.7 g, ˜100%) as a colorless liquid.

Workup

  1. filtrationThe solid was filtered
  2. concentrationthe filtrate concentrated
  3. customto give a solid
  4. filtrationThe solid was then filtered through a short silica gel column
  5. washeluting with 33% hexanes in ethyl ether
  6. customRemoval of solvents under reduced pressure

Sources & evidence

ORD record
ord-bc3d32a4c9b548e1a19243bd814c2610
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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