Methanol → 2-[8-(2-Methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutan-1-ol

HRID 252413Notes

Reaction equation

B.O1CCCC1.[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[CH:20]=[C:19]([CH2:22][CH:23]([CH:27]([CH3:29])[CH3:28])[C:24](O)=[O:25])[CH:18]=[CH:17]2.CO>O1CCCC1>[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[CH:20]=[C:19]([CH2:22][CH:23]([CH:27]([CH3:29])[CH3:28])[CH2:24][OH:25])[CH:18]=[CH:17]2

Participants

Conditions

Temperature: 0 °C

Procedure

3 ml of borane-tetrahydrofuran complex (1M in tetrahydrofuran) are added dropwise at 0° C. to the solution of 0.32 g of 2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyric acid in 2 ml of tetrahydrofuran. After 2 hours at room temperature, the reaction mixture is cooled to 0° C., admixed cautiously with 5 ml of methanol and subsequently stirred at room temperature for 1 hour. The reaction mixture is concentrated by evaporation—the residue is dissolved once again in methanol and concentrated by evaporation to dryness. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F).

Workup

concentrationThe reaction mixture is concentrated by evaporation—the residue
dissolutionis dissolved once again in methanol
concentrationconcentrated by evaporation to dryness

Sources & evidence

ORD record: ord-22f394face5f44b8bf62ce627bded2b0
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868036B2

Reaction notes

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