Cesium carbonate → (1R,2R,4aS,8aS)-1-{[(3-methoxy-5-methylphenyl)sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

HRID 422131Notes

Reaction equation

HRID 422131 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:10])[CH:6]=[C:7]([CH3:9])[CH:8]=1.CS(O[CH2:16][C@@H:17]1[C@:26]2([CH3:27])[C@H:21]([C:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][CH2:25]2)[CH2:20][CH2:19][C@:18]1([OH:31])[CH3:30])(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:10][CH2:16][C@@H:17]2[C@:26]3([CH3:27])[C@H:21]([C:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][CH2:25]3)[CH2:20][CH2:19][C@@:18]2([CH3:30])[OH:31])[CH:6]=[C:7]([CH3:9])[CH:8]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 225047193-Methoxy-5-methylbenzenethiolHCID 58294786((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl methanesulfonate

Product 1

HCID 66673229(1R,2R,4aS,8aS)-1-{[(3-methoxy-5-methylphenyl)sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-olYield 74.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-methoxy-5-methylbenzenethiol (11) (3.14 g, 20.4 mmol), ((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl methanesulfonate (12) (6.48 g, 20.4 mmol), and Cs2CO3 (19.90 g, 61.08 mmol) in CH3CN (300 mL) was stirred at room temperature for 1 h, then refluxed for 24 h. After cooling, the mixture was concentrated. Purification by chromatography on silica gel (Hexanes/EtOAc, 4:1) gave (1R,2R,4aS,8aS)-1-{[(3-methoxy-5-methylphenyl)sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (13) (5.70 g, purity ˜75%) as a yellow sticky mass.

Workup

  1. temperaturerefluxed for 24 h
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. customPurification by chromatography on silica gel (Hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-7577be6d9f244cc3bcf86d2f7e3f285e
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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