HCID 121396395, compound → 1-[(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydro furo[2,3-d][1,3]dioxol-5-yl]ethanol

HRID 60723Notes

Reaction equation

[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]2[O:7][C@H:8]([CH:10]=[O:11])[CH2:9][C@@H:4]2[O:3]1.[CH3:13][Mg]Br>C1COCC1>[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]2[O:7][C@H:8]([CH:10]([OH:11])[CH3:13])[CH2:9][C@@H:4]2[O:3]1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of (3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde (compound 25f, 800 mg, 1 mmol) in THF (20 mL) was added methyl magnesium bromide (2M in THF, 0.7 mL, 1.4 mmol) at −20° C. under argon. After being stirred at −20° C. for 20 hours, the reaction was quenched by saturated NH4Cl solution, extracted with EtOAc (30 mL) three times. The organic layers were combined and concentrated in vacuo to afford 400 mg crude product of 1-[(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydro furo[2,3-d][1,3]dioxol-5-yl]ethanol (compound 25g), which was used in next step without further purification. MS obsd. (ESI+) [(M+NH4)+]: 206.

Workup

customthe reaction was quenched by saturated NH4Cl solution
extractionextracted with EtOAc (30 mL) three times
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6f2566896aec47099a87873c6f1bacdd
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09441008B2

Reaction notes

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