Methyl Bromide → HCID 70638503, compound

HRID 259191Notes

Reaction equation

HRID 259191 reaction equation
[O:1]=[C:2]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:3]=[CH:4][C:5]1[CH:6]=[C:7]([OH:22])[C:8]2[CH:13]3[CH2:14][C:15]([CH3:18])=[CH:16][CH2:17][CH:12]3[C:11]([CH3:20])([CH3:19])[O:10][C:9]=2[CH:21]=1.[CH3:28][Mg]Br.CBr.[Mg]>C(OCC)C>[OH:1][C:2]([CH3:28])([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:3]=[CH:4][C:5]1[CH:6]=[C:7]([OH:22])[C:8]2[CH:13]3[CH2:14][C:15]([CH3:18])=[CH:16][CH2:17][CH:12]3[C:11]([CH3:19])([CH3:20])[O:10][C:9]=2[CH:21]=1

Participants

6

Reactant 4

HCID 6323Methyl BromideHCID 5462224MagnesiumHCID 68117058HCID 68117058, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 70638503HCID 70638503, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1.0 g (0.0028 mole) of 3-(3-oxo-1-octenyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol in diethyl ether was added dropwise to a solution of methyl magnesium bromide in ether prepared by bubbling methyl bromide into 0.78 g (0.032 mole) of magnesium. After the addition was complete, the mixture was refluxed for 3 hours and then decomposed by the careful addition of a mixture of methanol/diethyl ethr followed by dilute acid. The ethereal layer was separated and washed consecutively with water, 5% sodium bicarbonate and again water. It was dried and evaporated to leave 0.95 g of a gum which was chromatographed on magnesium silicate and eluted with graded mixtures of ether/petroleum ether. This furnished 0.28 g of 3-(3-hydroxy-3-methyl-1-octenyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol as a resinous material. The infrared and nuclear magnetic resonance spectra were consistent with the structure of the desired hydroxy compound.

Workup

  1. customprepared
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for 3 hours
  4. additiondecomposed by the careful addition of a mixture of methanol/diethyl
  5. additionby dilute acid
  6. customThe ethereal layer was separated
  7. washwashed consecutively with water, 5% sodium bicarbonate and again water
  8. customIt was dried
  9. customevaporated

Sources & evidence

ORD record
ord-63f2eaf9599545a79eac939168a5a299
Source dataset
uspto-grants-1977_07
Patent number
US04036857

Reaction notes

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