Heptanoic acid, 6-oxo-, methyl ester → (R)-methyl 6-hydroxyheptanoate

HRID 628941Notes

Reaction equation

HRID 628941 reaction equation
O1CCCC1.B.[O:7]=[C:8]([CH3:17])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]>C1(C)C=CC=CC=1>[OH:7][C@H:8]([CH3:17])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 288022Heptanoic acid, 6-oxo-, methyl esterHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 118036747(R)-methyl 6-hydroxyheptanoateYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

(S)-methyloxazaborolidine (8.77 g, 31.63 mmol) dissolved in 30 mL of toluene. The solution was cooled to 0° C. and the borane tetrahydrofuran complex (31.6 mL of 1.0M solution in THF, 31.6 mmol) was added. After 30 min the ketone 24 (5.0 g, 31.63 mmol) was added. The reaction solution was stirred for 4 h and was then quenched by slow addition of saturated aqueous ammonium chloride. The resultant mixture was extracted with EtOAc (2×). The combined organic portions were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Flash column chromatography (silica gel, 3:1 hex/EtOAc) afforded 2.58 g (51%) of the alcohol 25 (see scheme 4).

Workup

  1. customwas then quenched by slow addition of saturated aqueous ammonium chloride
  2. extractionThe resultant mixture was extracted with EtOAc (2×)
  3. washThe combined organic portions were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-661c1355917d4907b5abac8407e8f3fe
Source dataset
uspto-grants-2016_04
Patent number
US09315486B2

Reaction notes

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