Triethylamine → HCID 20245338, compound

HRID 482667Notes

Reaction equation

HRID 482667 reaction equation
[CH:1]([CH:3]([OH:11])[CH2:4][CH2:5][CH:6]1[O:10][CH2:9][CH2:8][O:7]1)=[CH2:2].CN(C1C=CC=CN=1)C.C(N(CC)CC)C.[C:28]([Si:32](Cl)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH3:31])([CH3:30])[CH3:29]>ClCCl.CN(C)C=O>[CH3:31][C:28]([Si:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[O:11][CH:3]([CH:1]=[CH2:2])[CH2:4][CH2:5][CH:6]1[O:10][CH2:9][CH2:8][O:7]1)([CH3:29])[CH3:30]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 94078tert-ButyldiphenylchlorosilaneHCID 20245336HCID 20245336, compound

Product 1

HCID 20245338HCID 20245338, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of α-ethenyl-1,3-dioxolane-2-propanol (49.4 g, 315 mmole) in dichloromethane (175 ml) was treated sequentially with dimethylaminopyridine (5.72 g, 47 mmole) and triethylamine (52.8 ml, 380 mmole) followed by (dropwise) a solution of t-butylchlorodiphenylsilane (89.5 g, 332 mmole) in dimethylformamide (150 ml). The reaction was stirred under argon for 48 hours (25° C.), poured into 2.5 L of ice water and extracted with ethyl acetate (1.2 L). The organic extracts were wsashed with water (2×1 L), brine (1 L), dried (sodium sulfate), filtered, and concentrated in vacuo to 130 g of viscous yellow oil. The crude product was dissolved in ether, filtered from a small amount of suspended material, concentrated in vacuo, and chromatographed (Waters, Prep 500 L.C., 10% ethyl acetate:hexane) to afford 106 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate (1.2 L)
  2. dry with materialdried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to 130 g of viscous yellow oil
  5. dissolutionThe crude product was dissolved in ether
  6. filtrationfiltered from a small amount of suspended material
  7. concentrationconcentrated in vacuo
  8. customchromatographed (Waters, Prep 500 L.C., 10% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-b9892401aab74683a4559cb1f37a3570
Source dataset
uspto-grants-1986_03
Patent number
US04574153

Reaction notes

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