Ethyl Acetate → HCID 11507368, compound

HRID 2103052Notes

Reaction equation

HRID 2103052 reaction equation
[CH2:1]([C:3]1[C:15]([OH:16])=[C:14]([CH2:17][CH3:18])[C:13]([CH:19]=[O:20])=[C:12]2[C:4]=1[CH2:5][CH2:6][C:7]1([O:11]2)[CH2:10][CH2:9][CH2:8]1)[CH3:2].[BH4-].[Na+].C(OCC)(=O)C>CO.CCCCCC>[CH2:1]([C:3]1[C:15]([OH:16])=[C:14]([CH2:17][CH3:18])[C:13]([CH2:19][OH:20])=[C:12]2[C:4]=1[CH2:5][CH2:6][C:7]1([O:11]2)[CH2:10][CH2:9][CH2:8]1)[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 86605494HCID 86605494, compound

Product 1

HCID 11507368HCID 11507368, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

To a solution of 5,7-diethyl-6-hydroxyspiro[chroman-2,1′-cyclobutane]-8-carbaldehyde (160 mg) prepared as described herein, in methanol (10 mL) was added excess of sodium borohydride and stirred at room temperature for 2 hours. Work up and chromatography (silica gel, ethyl acetate in hexane 5% to 15%) gave 130 mg of product. 1H-NMR (300 MHz, CDCl3) δ=4.80-4.70 (m, 3H), 2.85-2.55 (m, 7H), 2.30-1.60 (m, 8H), 1.20-1.10 (m, 6H) ppm. 13C-NMR (75 MHz, CDCl3) δ=146.3, 144.7, 128.2, 127.8, 124.7, 118.1, 76.9, 58.0, 34.2, 29.3, 19.6, 15.3, 13.4, 12.6 ppm. MS (m/z)=259 (100, M−OH)+.

Sources & evidence

ORD record
ord-dfab9af533854070ac7dae36cf0056f6
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

Loading…