(3aR,5S,6aR)-2,2-Dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde → HCID 121396357, compound

HRID 60693Notes

Reaction equation

HRID 60693 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.[CH2:13]([Mg]Br)[CH3:14]>C1COCC1>[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]2[O:7][C@H:8]([CH:10]([OH:11])[CH2:13][CH3:14])[CH2:9][C@H:4]2[O:3]1

Participants

4

Reactant 2

HCID 10910018(3aR,5S,6aR)-2,2-Dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde2×HCID 178418443HCID 178418443, compound

Product 1

HCID 121396357HCID 121396357, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of (3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde (compound 1d, 296 mg, 2 mmol) in THF (20 mL) was added ethyl magnesium bromide (2M in THF, 2 mL, 2 mmol) at −20° C. under argon. After being stirred at −20° C. for 20 hours, the reaction was quenched by saturated NH4Cl solution and extracted with EtOAc (30 mL) three times. The combined organic layers were concentrated in vacuo to afford the crude product of 1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propan-1-ol (compound 1e), which was used in next step without further purification. MS obsd. (ESI+) [(M+NH4)+]: 316.

Workup

  1. customthe reaction was quenched by saturated NH4Cl solution
  2. extractionextracted with EtOAc (30 mL) three times
  3. concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-320865cd4ba74b9285be8854a1030c5c
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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