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

HRID 441138Notes

Reaction equation

HRID 441138 reaction equation
[CH3:1][C@@H:2]([CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])[CH2:3][CH2:4][CH2:5]N1C(=O)C2N(C)C=NC=2N(C)C1=O.[Mg].II.C(Br)C[C@H](CCC=C(C)C)C.C=[O:40].[Cl-].[NH4+]>O1CCCC1>[CH3:1][C@@H:2]([CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])[CH2:3][CH2:4][CH2:5][OH:40]

Participants

8

Reactant 6

HCID 712FormaldehydeHCID 807IodineHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 10900106(S)-(+)-Citronellyl bromideHCID 228614871-(4-(S)-Methyl-8-methylnon-7-enyl)-3,7-dimethylxanthine

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

This example illustrates the synthesis of 1-(4-(S)-Methyl-8-methylnon-7-enyl)-3,7-dimethylxanthine (CT2536S). 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 min and the reaction stirred for a further 30 min after the addition was complete. The solution was added via a canula over 5 min to a suspension of paraformaldehyde (1.80 g, 60.0 mmol) in tetrahydrofuran (15 ml) and stirred at 25° C. for 6 hr. 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 give 4-(S)-methyl-8-methylnon-7-enyl alcohol as a clear liquid (3.25 g, 84%).

Workup

  1. additionafter the addition
  2. stirringstirred at 25° C. for 6 hr
  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-b9ee185662794b46b051f025c4479277
Source dataset
uspto-grants-1996_05
Patent number
US05521315

Reaction notes

Loading…