Sulfuric Acid → 4-(6-Cyclohexyl-1-hydroxyhexyl)-2-trimethylsilylfuran

HRID 654898Notes

Reaction equation

HRID 654898 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Mg]Br)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.BrCCCCCC1CCCCC1.[Mg].BrCCBr.[CH3:31][Si:32]([CH3:41])([CH3:40])[C:33]1[O:37][CH:36]=[C:35]([CH:38]=[O:39])[CH:34]=1.S(=O)(=O)(O)O>O1CCCC1>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:38]([C:35]2[CH:34]=[C:33]([Si:32]([CH3:41])([CH3:40])[CH3:31])[O:37][CH:36]=2)[OH:39])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 6

HCID 1118Sulfuric AcidHCID 78391,2-DibromoethaneHCID 5462224MagnesiumHCID 14952366(5-Bromopentyl)cyclohexaneHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178419675HCID 178419675, compound

Product 1

HCID 198859104-(6-Cyclohexyl-1-hydroxyhexyl)-2-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 5-cyclohexylpentyl-magnesium bromide (1.32 mmol, prepared from 0.31 g., 1.32 mmol 1-bromo-5-cyclohexylpentane and 2.88 mmol magnesium, with a catalytic amount of 1,2-dibromoethane as initiator), in 2.5 ml anhydrous tetrahydrofuran at 0° under argon was added dropwise 5-trimethylsilyl-3-furaldehyde (0.23 g., 1.40 mmol) in 2.5 ml tetrahydrofuran. This solution was allowed to warm to room temperature, stirred for one hour, and then poured over crushed ice containing several drops of concentrated sulfuric 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 (0.173 g.). This material was purified by flash chromatography (silica, 90% petroleum ether/ethyl ether) 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 (0.173 g.)
  8. customThis material was purified by flash chromatography (silica, 90% petroleum ether/ethyl ether)

Sources & evidence

ORD record
ord-7168d46f87ff4d4ab3382c12e0767a97
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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