4-Bromostyrene → HCID 90409758, compound

HRID 630575Notes

Reaction equation

HRID 630575 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[Mg].C([C@@H]1CC[C@@H](C)C[C@H]1O[C:22](=[O:36])[C:23]([O:25][C@@H:26]1[CH2:31][C@H:30]([CH3:32])[CH2:29][CH2:28][C@H:27]1[CH:33]([CH3:35])[CH3:34])=[O:24])(C)C.[NH4+].[Cl-]>C1COCC1.CCCCCCC.CCOCC>[O:36]=[C:22]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1)[C:23]([O:25][C@@H:26]1[CH2:31][C@H:30]([CH3:32])[CH2:29][CH2:28][C@H:27]1[CH:33]([CH3:34])[CH3:35])=[O:24]

Participants

7

Reactant 4

HCID 162634-BromostyreneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 11383005Ethanedioic acid, 1,2-bis[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl] ester, rel-

Product 1

HCID 90409758HCID 90409758, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21897273Diethylether heptaneSolvent2×

Procedure

A Grignard reagent prepared from 4-bromostyrene (2.75 g, 15.0 mmol) and magnesium (0.39 g, 16.0 mmol) in THF (20 mL) was added dropwise (during a period of 20 min) to a stirred solution of bis[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxalate (5.00 g, 13.7 mmol) in THF (15 mL) at −60° C. The mixture was left warming to room temperature and poured into a mixture of ice (200 g) and a saturated solution of NH4Cl (10 mL). Extraction with diethyl ether (2×), washing with water (3×), drying (Na2SO4) and concentrating afforded 6.42 g of the crude compound as an oil. Repetitive column chromatography (SiO2, heptane/ether 7:3 and heptane/ether 95:5) gave 2.03 g (47%) of an oil.

Workup

  1. waitThe mixture was left
  2. extractionExtraction with diethyl ether (2×)
  3. washwashing with water (3×)
  4. dry with materialdrying (Na2SO4)
  5. concentrationconcentrating
  6. customafforded 6.42 g of the crude compound as an oil

Sources & evidence

ORD record
ord-8fc21dd5151147c583f118e4e65f5cff
Source dataset
uspto-grants-2016_04
Patent number
US09315763B2

Reaction notes

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