Sodium Carbonate → {8-Fluoro-1,4-dioxaspiro[4.5]decan-8-yl}methanol

HRID 573212Notes

Reaction equation

HRID 573212 reaction equation
[FH:1].N1C=CC=CC=1.O1[C:10]2([CH2:19][CH2:18][CH2:17][CH2:16][C:13]3([O:15][CH2:14]3)[O:12][CH2:11]2)C1.[C:20]([O-:23])([O-])=O.[Na+].[Na+]>ClCCl>[F:1][C:18]1([CH2:20][OH:23])[CH2:17][CH2:16][C:13]2([O:12][CH2:11][CH2:14][O:15]2)[CH2:10][CH2:19]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 64774Pyridine, hydrofluoride (1:1)HCID 86647914HCID 86647914, compoundHCID 178435160HCID 178435160, compound

Product 1

HCID 67225989{8-Fluoro-1,4-dioxaspiro[4.5]decan-8-yl}methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of pyridine hydrofluoride (4 g) in dichloromethane (10 mL) was added dropwise to a solution of EXAMPLE 443A (1.7 g) in dichloromethane (20 mL) in a polyethylene bottle at 0° C. The mixture was stirred at room temperature overnight. The mixture was carefully poured over a mixture of ice-water and Na2CO3 and extracted with ethyl acetate (2×300 mL). After washing with water and brine, the organic layer was dried over Na2SO4, and filtered. Concentration of the filtrate gave the crude product.

Workup

  1. extractionextracted with ethyl acetate (2×300 mL)
  2. washAfter washing with water and brine
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-be6fec7e800449769b81bcf00e38a8c0
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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