Water → HCID 57757027, compound

HRID 1673180Notes

Reaction equation

HRID 1673180 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C@H:12]1[CH2:16][O:15]C(C)(C)[O:13]1)[CH2:6][CH2:5]2.O>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C@H:12]([OH:13])[CH2:16][OH:15])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 962WaterHCID 58400517HCID 58400517, compound

Product 1

HCID 57757027HCID 57757027, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

6-Fluoro-3,4-dihydro-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2H-chromene (40 mg, 0.16 mmol, diastereomeric ratio 75:25) was dissolved in acetic acid (2 ml) and demi water (0.7 ml). The reaction mixture was stirred vigorously and heated to 65° C. After 3 h at 65° C. the reaction mixture was cooled to 25° C. The solution was then concentrated in vacuo at 35° C. to obtain (R)-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-ethane-1,2-diol as a vetrous oil (89% yield, diastereomeric ratio 73:27).

Workup

  1. temperatureAfter 3 h at 65° C. the reaction mixture was cooled to 25° C
  2. concentrationThe solution was then concentrated in vacuo at 35° C.

Sources & evidence

ORD record
ord-62101eb60272416aae8ea4cc298488f8
Source dataset
uspto-grants-2011_08
Patent number
US07999124B2

Reaction notes

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