Water → HCID 18600864, compound

HRID 638020Notes

Reaction equation

HRID 638020 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[Mg]Br.[O:16]1[C@:20]([CH3:37])([CH2:21][CH2:22][CH2:23][C@H:24]([CH3:36])[CH2:25][CH2:26][CH2:27][C@H:28]([CH3:35])[CH2:29][CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[C@@H:17]1[CH:18]=[O:19].O>O1CCCC1>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH:18]([OH:19])[C@H:17]1[O:16][C@:20]1([CH3:37])[CH2:21][CH2:22][CH2:23][C@H:24]([CH3:36])[CH2:25][CH2:26][CH2:27][C@H:28]([CH3:35])[CH2:29][CH2:30][CH2:31][CH:32]([CH3:33])[CH3:34]

Participants

5

Reactant 3

HCID 962WaterHCID 53653529HCID 53653529, compoundHCID 178490459HCID 178490459, compound

Product 1

HCID 18600864HCID 18600864, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 mmol of 2,5-dimethoxy-3,4,6-trimethylphenylmagnesium bromide in 2 ml of tetrahydrofuran was added dropwise at 0° C. while stirring to a solution of 300 mg (0.97 mmol) of (2R,3R,7R,11R)-2,3-epoxy-3,7,11,15-tetramethylhexadecanal in 10 ml of tetrahydrofuran. After completion of the dropwise addition, the mixture was stirred at room temperature for a further 3 hours. 20 ml of water weree then added and the mixture was extracted three times with 20 ml of ether each time. The combined organic phases were dried over sodium sulphate and concentrated on a rotary evaporator. The thus-obtained crude produce (502 mg) was chromatographed on silica gel with toluene/ethyl acetate (2:1 parts by volume) and there were obtained 448 mg(94%) of (1RS,2R,3R,7R, 11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2,3-epoxy-3,7,11,15-tetramethylhexadecanol, [α]D20 =-0.66° (c=1.51% in chloroform).

Workup

  1. additionAfter completion of the dropwise addition
  2. extractionthe mixture was extracted three times with 20 ml of ether each time
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe thus-obtained crude
  6. customproduce (502 mg)
  7. customwas chromatographed on silica gel with toluene/ethyl acetate (2:1 parts by volume)

Sources & evidence

ORD record
ord-320216e6f47a43d48185b81782291b04
Source dataset
uspto-grants-1985_12
Patent number
US04559407

Reaction notes

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