HCID 23507944, compound → HCID 23507950, compound

HRID 2258647Notes

Reaction equation

HRID 2258647 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9]3(OCC[O:13]3)[CH2:10]2)=[CH:5][CH:4]=1)#[CH:2]>C1COCC1.Cl.C(OCC)C>[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[CH2:10]2)=[CH:5][CH:4]=1)#[CH:2]

Participants

5

Reactant 1

HCID 23507944HCID 23507944, compound

Product 1

HCID 23507950HCID 23507950, compoundYield 46.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7'-ethynyl-3',4'-dihydrospiro[1,3-dioxolane-2,2'(1'H)-naphthalene] (0.85 g, 3.9 mmol) in THF (15 ml) and 1N HCl (5 ml) was stirred overnight at room temperature. Concentrated HCl (2×0.5 ml) was then added in two aliquots 2 hours apart. After stirring a further 2 hours the solution was diluted with diethyl ether, the aqueous phase was separated, and the solution dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel (15 g) eluting with diethyl ether:hexane (1:9→1:4) to give 7-ethynyl-2-tetralone as a solid (0.31 g). 1H NMR (CDCl3, 200 MHz) δ: 2.54 (t, J=7 Hz, 2H, CH2), 3.05 (s, 1H, ethynyl H), 3.06 (t, J=7 Hz, 2H, CH2), 3.56 (s, 2H, CH2), 7.18 (d, J=8 Hz, 1H, Ar), 7.26 (s, 1H, Ar), 7.34 (d, J=Hz, 1H, Ar).

Workup

  1. customthe aqueous phase was separated
  2. dry with materialthe solution dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (15 g)
  5. washeluting with diethyl ether:hexane (1:9→1:4)

Sources & evidence

ORD record
ord-8058f5b19fb947159df894266dc5b45a
Source dataset
uspto-grants-1997_08
Patent number
US05661155

Reaction notes

Loading…