Ethyl formate → Bis(1,3-benzodioxol-5-yl)methanol

HRID 2278159Notes

Reaction equation

C([Li])(C)(C)C.Br[C:7]1[CH:15]=[CH:14][C:10]2[O:11][CH2:12][O:13][C:9]=2[CH:8]=1.[O:16]1[C:20]2[CH:21]=[CH:22][C:23]([CH:25]=[O:26])=[CH:24][C:19]=2[O:18][CH2:17]1.C(OCC)=O>C1COCC1>[O:11]1[C:10]2[CH:14]=[CH:15][C:7]([CH:25]([C:23]3[CH:22]=[CH:21][C:20]4[O:16][CH2:17][O:18][C:19]=4[CH:24]=3)[OH:26])=[CH:8][C:9]=2[O:13][CH2:12]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirring solution of tert-butyllithium (1.8 mL, 3.1 mmol, 1.7M in pentane) at −78° C. was added dropwise a solution of 5-bromobenzo-1,3-dioxole (1.5 mmol) in THF (3 mL). After 30 min, benzo-1,3-dioxole-5-carbaldehyde (1.5 mmol) or ethyl formate (0.5 mmol) in THF (1 mL) was added. The mixture was stirred at −78° C. for 1 h and subsequently warmed to room temperature and stirred for an additional 4 h. The reaction was quenched by the addition of a saturated solution of NH4Cl and extracted with EtOAc (3×). The organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure. Purification of the crude oil by flash chromatography (20% EtOAc/hexanes) provided the diphenyl methanol product.

Workup

temperaturesubsequently warmed to room temperature
stirringstirred for an additional 4 h
customThe reaction was quenched by the addition of a saturated solution of NH4Cl
extractionextracted with EtOAc (3×)
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customPurification of the crude oil by flash chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record: ord-9ade824fd3dc46c290e2b1131dd91ea9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133148B2

Reaction notes

Loading…