Methane, dichloromethoxy- → HCID 86605494, compound

HRID 2103051Notes

Reaction equation

HRID 2103051 reaction equation
[CH2:1]([C:3]1[C:15]([OH:16])=[C:14]([CH2:17][CH3:18])[CH:13]=[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].[CH3:19][O:20]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[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)[CH2:8][CH2:9][CH2:10]1)[CH3:2]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 11622906HCID 11622906, compound

Product 1

HCID 86605494HCID 86605494, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5,7-diethylspiro[chroman-2,1′-cyclobutan]-6-ol (900 mg) in dichloromethane (5 mL) was added titanium tetrachloride (670 mg, 0.4 mL) and dichloromethyl methyl ether (505 mg, 0.39 mL). The solution was stirred at room temperature for 5 hours. The reaction was quenched using diluted hydrochloric acid. Work up and chromatography (silica gel, ethyl acetate in hexane 5%) gave 680 mg of 5,7-diethyl-6-hydroxyspiro[chroman-2,1′-cyclobutane]-8-carbaldehyde.

Workup

  1. customThe reaction was quenched

Sources & evidence

ORD record
ord-00d1d498f4c74bedb17aa755f3e96646
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

Loading…