4-tert-Butylcatechol → HCID 22645397, compound

HRID 2414278Notes

Reaction equation

HRID 2414278 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:28])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2OS(C(F)(F)F)(=O)=O)[CH:10]([CH3:29])[CH2:9]1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH:30]([Sn](CCCC)(CCCC)CCCC)=[CH2:31].[Cl-].[Li+].C(C1C=C(O)C(=CC=1)O)(C)(C)C>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:28])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:30]=[CH2:31])[CH:15]=2)[CH:10]([CH3:29])[CH2:9]1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 73814-tert-ButylcatecholHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 22645412HCID 22645412, compound

Product 1

HCID 22645397HCID 22645397, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-hexanoyl-3,4-dimethyl-4-(trifluoromethanesulfonyloxyphenyl)piperidine (Preparation 6, 3.0 g, 6.90 mmol) in tetrahydrofuran (30 mL) at room temperature were added sequentially vinyltributyltin (2.12 mL, 7.24 mmol), lithium chloride (585 mg, 13.8 mmol), and tetrakis(triphenylphosphine)palladium(0) (80 mg, 0.69 mmol). The mixture was heated to reflux under a nitrogen atmosphere for 1½ hours at which time a few crystals of 4-tert-butylcatechol were added. Heating at reflux was then continued for a further 16 hours. The mixture was cooled and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a gradient of ethyl acetate:hexane (1:10 to 1:3). The title compound was obtained as a clear oil (2.1 g).

Workup

  1. temperatureThe mixture was heated
  2. additionwere added
  3. temperatureHeating
  4. temperatureat reflux
  5. temperatureThe mixture was cooled
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with a gradient of ethyl acetate:hexane (1:10 to 1:3)

Sources & evidence

ORD record
ord-d8d507ec841143c59f9e1aa881ac67d3
Source dataset
uspto-grants-2004_11
Patent number
US06812236B2

Reaction notes

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