Hydrochloric Acid → HCID 53888854, compound

HRID 1084350Notes

Reaction equation

HRID 1084350 reaction equation
[F:1]/[C:2](=[CH:5]\[CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])/[CH:3]=[O:4].[C:16]([Mg]Br)#[CH:17].CCOCC.Cl>O1CCCC1.C(OCC)(=O)C.CCCCCC>[Si:9]([O:8][CH2:7][CH2:6][CH:5]=[C:2]([F:1])[CH:3]([OH:4])[C:16]#[CH:17])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 20063409HCID 20063409, compoundHCID 178418486HCID 178418486, compound

Product 1

HCID 53888854HCID 53888854, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

5.01 Grams of (Z)-2-fluoro-5-(tert-butyldimethylsilyloxy)-2-pentenal was dissolved in 20 ml of dry tetrahydrofuran, and to the resulting solution was added dropwise a tetrahydrofuran solution of ethynylmagnesium bromide (1.5 equivalents vs. the aldehyde) with ice-cooling. After addition, the solution was stirred at room temperature for 10 hours. The reaction solution was cooled with ice, and after adding 50 ml of ether, poured into 10% hydrochloric acid. The ether layer was separated, and the aqueous layer was extracted twice with ether. The ether extracts were combined with the above ether layer, and this mixture was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was then removed under reduced pressure. The residue obtained was treated by column chromatography on silica gel with an ethyl acetate/hexane (1:5) mixture as an eluent to obtain 3.42 g of 7-(tert-butyldimethylsilyloxy)-4-fluoro-3-hydroxy-4-hepten-1-yne as a pale yellow oily product.

Workup

  1. additionAfter addition
  2. temperatureThe reaction solution was cooled with ice
  3. customThe ether layer was separated
  4. extractionthe aqueous layer was extracted twice with ether
  5. washthis mixture was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was then removed under reduced pressure
  8. customThe residue obtained

Sources & evidence

ORD record
ord-ad8df0f630884d91aa8e76b92349fcf3
Source dataset
uspto-grants-1991_04
Patent number
US05004753

Reaction notes

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