Dichloromethane → HCID 18949909, compound

HRID 727954Notes

Reaction equation

HRID 727954 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:12])[C:9](Cl)=O.O[CH:15]([C:28]1[CH:32]=[C:31]([Si:33]([CH3:36])([CH3:35])[CH3:34])OC=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]C.[Cl:37]CCl>>[Cl:37][CH:28]([C:32]1[CH:9]=[CH:8][O:12][C:31]=1[Si:33]([CH3:36])([CH3:35])[CH3:34])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuran

Product 1

HCID 18949909HCID 18949909, compound

Procedure

Triethylamine (0.55 ml, 3.95 mmol), followed by oxalyl chloride (0.34 ml, 3.95 mmol) was added dropwise to a solution of 3-(1-hydroxytridecyl)-5-trimethylsilylfuran (890 mg, 2.63 mmol) in anhydrous dichloromethane (10 ml) at 0°. After 40 minutes, the reaction was quenched with ice water. Extraction (dichloromethane) and evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by flash chromatography on silica using 5% ethyl ether/hexane. Fractions with Rf of about 0.37 on evaporation gave 3-(1-chlorotridecyl)-2-trimethylsilylfuran as a pale yellow oil, solidified to a colorless solid on storage at -20°.

Workup

  1. customthe reaction was quenched with ice water
  2. extractionExtraction (dichloromethane) and evaporation of the
  3. dry with materialdried (magnesium sulfate)
  4. customextracts gave an oil, which
  5. customwas purified by flash chromatography on silica using 5% ethyl ether/hexane
  6. customFractions with Rf of about 0.37 on evaporation

Sources & evidence

ORD record
ord-3f74fb5f913b462681f08acae7560af1
Source dataset
uspto-grants-1991_09
Patent number
US05045564

Reaction notes

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