Hydrochloric Acid → HCID 53835839, compound

HRID 654895Notes

Reaction equation

HRID 654895 reaction equation
[CH3:1][C:2]([CH2:8][CH2:9][C:10]1[C:15]([CH3:17])([CH3:16])[CH2:14][CH2:13][CH2:12][C:11]=1[CH3:18])=[CH:3][CH2:4][CH2:5][Mg]Br.BrCCC=C(C)CCC1C(C)(C)CCCC=1C.[Mg].BrCCBr.[CH3:41][Si:42]([CH3:51])([CH3:50])[C:43]1[O:47][CH:46]=[C:45]([CH:48]=[O:49])[CH:44]=1.Cl>C(OCC)C>[OH:49][CH:48]([C:45]1[CH:44]=[C:43]([Si:42]([CH3:51])([CH3:50])[CH3:41])[O:47][CH:46]=1)[CH2:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:8][CH2:9][C:10]1[C:15]([CH3:17])([CH3:16])[CH2:14][CH2:13][CH2:12][C:11]=1[CH3:18]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 5462224MagnesiumHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 53956524HCID 53956524, compoundHCID 178445866HCID 178445866, compound

Product 1

HCID 53835839HCID 53835839, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 4-methyl-6-(2,6,6-trimethylcyclohex-1-enyl)-3-hexenylmagnesium bromide (0.70 mmol, prepared from 0.21 g., 0.70 mmol 1-bromo-4-methyl-6-(2,6,6-trimethylcyclohex-1-enyl)-3-hexene and 2.1 mmol magnesium, with a catalytic amount of 1,2-dibromoethane as initiator), in one ml ethyl ether at 0° under argon was added dropwise 5-trimethylsilyl-3-furaldehyde (0.13 g., 0.77 mmol) in one ml ether. This solution was allowed to warm to room temperature, stirred for 30 minutes, and then poured over crushed ice containing several drops of hydrochloric acid. The resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate. The organic portion was washed with water, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to give a colorless oil. This material was purified by flash chromatography (silica, 20% ethyl ether/hexane) to give the desired alcohol.

Workup

  1. additionpoured
  2. customThe resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate
  3. washThe organic portion was washed with water, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a colorless oil
  8. customThis material was purified by flash chromatography (silica, 20% ethyl ether/hexane)

Sources & evidence

ORD record
ord-ad13ac63edd04685aef731d1921e5051
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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