HCID 23507944, compound → HCID 23507950, compound

HRID 1883988Notes

Reaction equation

HRID 1883988 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, ethynylH), 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=8 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-c112eacab04541afb6b1b737a4944727
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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