Water → HCID 69155444, compound

HRID 1836908Notes

Reaction equation

HRID 1836908 reaction equation
[Br:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:8]([CH3:14])([CH3:13])[CH:7]=[CH:6][C:5]([CH3:16])([CH3:15])[C:4]=2[CH:3]=1.S(=O)(O)[O-:18].[Na+].[OH2:22]>N1C=CC=CC=1.[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:8]([CH3:14])([CH3:13])[C@@H:7]([OH:22])[C@@H:6]([OH:18])[C:5]([CH3:16])([CH3:15])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 109568496-Bromo-1,1,4,4,7-pentamethyl-1,4-dihydronaphthaleneHCID 23665763Sodium Bisulfite

Product 1

HCID 69155444HCID 69155444, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 9.41 g (33.7 mmol) of 2-bromo-3,5,5,8,8-pentamethyl-5,8-dihydronaphthalene in 110 ml pyridine was added 8.65 g (34.0 mmol) osmium tetroxide under an atmosphere of nitrogen. After stirring at room temperature for 18 hours, 17.3 g (166 mmol) of sodium bisulfite in 110 ml water was added. After 2 hours the resulting solution was partitioned between ethyl acetate and aqueous hydrochloric acid. The organic layer was washed with water, washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude material was purified by flash chromatography with elution with 30% ethyl acetate/hexane to yield 7.97 g (75%) of 2-bromo-cis-6,7-dihydroxy-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene as a white solid (M+=312).

Workup

  1. customAfter 2 hours the resulting solution was partitioned between ethyl acetate and aqueous hydrochloric acid
  2. washThe organic layer was washed with water
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography with elution with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7179cd60538e46cd89603f9e9f883d28
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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