Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1903583Generated: October 25, 2026

Diethyl Ether → 8-Methoxychromane-6-carbaldehyde

https://huagongshe.com/reaction/1903583

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantDimethylformamideHCID 6228—
ReactantBromo-methoxy-chromanHCID 20193557—
ReactantButyllithiumHCID 178418339—
SolventDiisopropyl EtherHCID 7914—
Product8-Methoxychromane-6-carbaldehydeHCID 1283198351%

Reaction Conditions

Temperature-50 °C

Reaction Steps

The procedure is as according to the method described for preparation III, but maintaining the temperature at -50° C. From 186 g (7.7×10-1M) of bromo-methoxy-chroman Ib2 in 500 cm3 of anhydrous ether and 7.7×10-1M of n-butyllithium in 650 cm3 of anhydrous ether, and after addition of 78 g (1.1 M) of N,N-dimethylformamide in 200 cm3 of anhydrous ether and recrystallisation in isopropyl ether, 75 g (yield=51%) of expected compound are isolated. m.p.=81° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04436915
Source datasetuspto-grants-1984_03
ORD IDord-f86e1d0a8a474c68a8f22ae9ab89240b
Source noteuspto-grants-1984_03