Water → 7-Methoxy-1-heptanol

HRID 862978Notes

Reaction equation

HRID 862978 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](O)=[O:10].B.O.C([O-])([O-])=O.[K+].[K+]>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6331BoraneHCID 11430Potassium CarbonateHCID 154095287-Methoxyheptanoic Acid

Product 1

HCID 154095297-Methoxy-1-heptanolYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the title product of Example 2 (18.3 g, 114 mmol) in 60 mL of tetrahydrofuran at 0 ° C. was added dropwise a solution of borane in tetrahydrofuran (175 mL, 1M). After stirring at room temperature for 3 days, 300 mL of water was added followed by solid K2CO3 (31.7 g, 229 mmol). The layers were separated and the aqueous phase extracted with three portions of diethyl ether. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by distillation at reduced pressure (8 mm Hg) to give the title compound (12 g), b.p. 107°-110° C. The structure was verified by NMR.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase extracted with three portions of diethyl ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationThe crude product was purified by distillation at reduced pressure (8 mm Hg)

Sources & evidence

ORD record
ord-16a5c14a1aef4584ab1e0962926c638f
Source dataset
uspto-grants-1998_02
Patent number
US05719290

Reaction notes

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