1,3-Dithiane → HCID 14652366, compound

HRID 2352505Notes

Reaction equation

HRID 2352505 reaction equation
[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH2:2]1.[Li]CCCC.[C:12]1([C:18]([CH2:20][CH2:21][C:22]#[CH:23])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCCC1.CCCCCC>[OH:19][C:18]([CH:2]1[S:3][CH2:4][CH2:5][CH2:6][S:1]1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:20][CH2:21][C:22]#[CH:23]

Participants

6

Reactant 3

HCID 104511,3-DithianeHCID 12487496HCID 12487496, compoundHCID 178418339Butyllithium

Product 1

HCID 14652366HCID 14652366, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

1,3-Dithiane (3.8 g, 31.6 mmol) was stirred in 120 mL of tetrahydrofuran at -40° C. under argon and 13.2 g (33 mmol) of 2.5M n-BuLi in hexane was added. After 10 minutes the temperature was adjusted to -20° C. and 1.25 hours later 2.27 g (14.36 mmol) of but-3-ynyl phenyl ketone was added as a solid. Stirring was continued for 20 minutes before placing in a freezer at -20° C. for 20 hours. The mixture was then poured onto water, the layers were separated, and the aqueous portion extracted with methylene chloride (3×30 mL). The combined organics were washed with brine, dried (MgSO4) and solvents evaporated at reduced pressure. The residue was chromatographed on 75 g silica (98:2, hexane:EtAc, then 4%, 10%, and 20% EtAc) to give 3.0 g (75%) of product.

Workup

  1. waitwas continued for 20 minutes
  2. waitbefore placing in a freezer at -20° C. for 20 hours
  3. additionThe mixture was then poured onto water
  4. customthe layers were separated
  5. extractionthe aqueous portion extracted with methylene chloride (3×30 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried (MgSO4) and solvents
  8. customevaporated at reduced pressure
  9. customThe residue was chromatographed on 75 g silica (98:2, hexane

Sources & evidence

ORD record
ord-f65d66992cd24db99e9a92447cdcc550
Source dataset
uspto-grants-1989_10
Patent number
US04877779

Reaction notes

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