Formaldehyde → 4-(S)-methyl-8-methylnon-7-enyl alcohol

HRID 361535Notes

Reaction equation

HRID 361535 reaction equation
[Mg].II.[CH2:4](Br)[CH2:5][C@H:6]([CH2:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH3:7].[CH2:15]=[O:16].[Cl-].[NH4+]>O1CCCC1>[CH3:7][C@@H:6]([CH2:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH2:5][CH2:4][CH2:15][OH:16]

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 807IodineHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 10900106(S)-(+)-Citronellyl bromide

Product 1

HCID 111712294-(S)-methyl-8-methylnon-7-enyl alcoholYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

This example illustrates a synthesis of 1-(4-(S)-Methyl-7,8-oxido-8-methylnonyl)-3,7-dimethylxanthine (inventive compound no. 2548S). To a suspension of magnesium (2.74 g, 140 mmol) and a crystal of iodine in tetrahydrofuran (15 mL) was added (S)-citronellyl bromide (5.0 g, 22.8 mmol) in tetrahydrofuran (10 mL) over 30 minutes and the reaction stirred for a further 30 minutes after the addition was complete. The solution was added via a canula over 5 minutes to a suspension of paraformaldehyde (1.80 g, 60.0 mmol) in tetrahydrofuran (15 mL) and stirred at 25° C. for 6 hours. Saturated ammonium chloride (40 mL) was added and extracted with diethyl ether (2×30 mL). The combined organic extracts were dried (magnesium sulfate) and evaporated to yield 3.25 g (84% yield) 4-(S)-methyl-8-methylnon-7-enyl alcohol as a clear liquid.

Workup

  1. additionafter the addition
  2. stirringstirred at 25° C. for 6 hours
  3. extractionextracted with diethyl ether (2×30 mL)
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-974998121ae44ab7a222725b6c5d4b5d
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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