Hydrochloric Acid → HCID 18624262, compound

HRID 1385213Notes

Reaction equation

HRID 1385213 reaction equation
[Mg].II.Br[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1.[CH:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[C:14]1=[O:23])[CH2:20]2.Cl>C1COCC1>[CH2:6]([C:7]1[CH:8]=[C:9]([C:14]2([OH:23])[CH:15]3[CH2:21][CH:19]4[CH2:18][CH:17]([CH2:22][CH:13]2[CH2:20]4)[CH2:16]3)[CH:10]=[CH:11][CH:12]=1)[CH3:5]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 7666Phenethyl bromideHCID 64151AdamantanoneHCID 5462224Magnesium

Product 1

HCID 18624262HCID 18624262, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirring mixture of magnesium turnings (0.89 g, 36.6 mmol) and iodine (catalytic) in dry THF (60 mL) was treated with 3-bromoethylbenzene (5 ML, 36.6 mmol), refluxed for 3 h, cooled to room temperature, treated with a solution of 2-adamantanone (5.0 g, 33.3 mmol) in dry THF (20 mL) and refluxed for 2 h. The mixture was cooled to room temperature, treated with 3-M HCl (20 mL), extracted with EtOAc (2×20 mL), the combined extracts were washed with water (10 mL), dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; heptane-EtOAc (9:1)] to give the product (7.84 g, 92%) as a white solid: mp 63-65° C.; IR νmax (Nujol)/cm−1 3442, 3281, 2921, 2855, 1604, 1451, 1101, 1043, 1009, 803 and 708; NMR δH (400 MHz, CDCl3) 1.23 (3H, t, J 7.5 Hz), 1.61-1.70 (9H, m), 1.89 (1H, s), 2.38-2.41 (2H, m), 2.56 (2H,s), 2.65 (2H, q, J7.5 Hz), 3.46 (1H, s), 7.11 (1H, d, J7.5 Hz) and 7.24-7.36 (3H, m); Anal. Calcd for C18H24O: C, 84.32; H, 9.43. Found: C, 84.24; H, 9.28.

Workup

  1. temperaturerefluxed for 3 h
  2. temperaturerefluxed for 2 h
  3. temperatureThe mixture was cooled to room temperature
  4. extractionextracted with EtOAc (2×20 mL)
  5. washthe combined extracts were washed with water (10 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. custompurified by chromatography [SiO2; heptane-EtOAc (9:1)]

Sources & evidence

ORD record
ord-336ae1f146a14f50b5fa145546bb07d7
Source dataset
uspto-grants-2001_07
Patent number
US06262106B1

Reaction notes

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