2,6-Di-tert-butyl-4-methylphenol → HCID 68638350, compound

HRID 641579Notes

Reaction equation

HRID 641579 reaction equation
[CH2:1]([O:8][C:9](=[O:32])[NH:10][CH:11]1[CH2:20][CH2:19][C:14]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:13][CH:12]1[CH2:21][S:22]([C:25]1[CH:30]=[CH:29][C:28](Br)=[CH:27][CH:26]=1)(=[O:24])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33](C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)[CH3:34]>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:32])[NH:10][C@H:11]1[CH2:20][CH2:19][C:14]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:13][C@H:12]1[CH2:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH:33]=[CH2:34])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 68469843HCID 68469843, compound

Product 1

HCID 68638350HCID 68638350, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

[7-(4-Bromo-benzenesulfonylmethyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-carbamic acid benzyl ester from example (3e) (1.0 g), was dissolved in toluene (15 ml) prior to the addition of PdCl2(PPh3)2 (66 mg) and Sn(vinyl)Bu3 (0.61 ml), and a few crystals of 2,6-di-tert-butyl-4-methylphenol. The resulting solution was heated to reflux for 4 h. After cooling, the solution was concentrated. Flash chromatography of the resulting residue gave (7R,8S) [7-(4-vinyl-benzenesulfonylmethyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-carbamic acid benzyl ester (668 mg). MS found: (M+H)+=460.3.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 4 h
  3. temperatureAfter cooling
  4. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-4910358b8a0645bd9689c9a2d174f504
Source dataset
uspto-grants-2010_04
Patent number
US07696205B2

Reaction notes

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