(S)-6-Ethyl-1,4-dioxaspiro[4.5]decane-6-propanoic Acid, 2-Hydroxyethyl Ester → (S)-6-Ethyl-alpha,alpha-diphenyl-1,4-dioxaspiro[4.5]decane-6-propanol

HRID 247650Notes

Reaction equation

HRID 247650 reaction equation
[CH2:1]([C@@:3]1([CH2:13][CH2:14][C:15]([O:17]CCO)=O)[CH2:12][CH2:11][CH2:10][CH2:9][C:4]21[O:8][CH2:7][CH2:6][O:5]2)[CH3:2].[C:21]1([Mg]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCOCC>[CH2:1]([C@@:3]1([CH2:13][CH2:14][C:15]([C:3]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:4]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[OH:17])[CH2:12][CH2:11][CH2:10][CH2:9][C:4]21[O:5][CH2:6][CH2:7][O:8]2)[CH3:2]

Participants

4

Reactant 2

HCID 56993252(S)-6-Ethyl-1,4-dioxaspiro[4.5]decane-6-propanoic Acid, 2-Hydroxyethyl Ester2×HCID 178418255HCID 178418255, compound

Product 1

HCID 54110677(S)-6-Ethyl-alpha,alpha-diphenyl-1,4-dioxaspiro[4.5]decane-6-propanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

(S)-6-Ethyl-1,4-dioxaspiro[4.5]decane-6-propanoic acid, 2-hydroxyethyl ester (one half of the material produced in step (d), 460 g) was diluted to 1 L with anhydrous ether and added dropwise (quickly, almost as a slow stream) to a solution of phenylmagnesium bromide (5.05 mol, 1.68 L of a 3M solution) in ether at 0° C. After 5 minutes the reaction was quenched with 1M hydrochloric acid until all of the salts dissolved. The mixture was extracted with ether (3×500 mL), dried over magnesium sulfate, and concentrated to a yellow oil (175 g, some material was lost in workup).

Workup

  1. customAfter 5 minutes the reaction was quenched with 1M hydrochloric acid until all of the salts
  2. dissolutiondissolved
  3. extractionThe mixture was extracted with ether (3×500 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to a yellow oil (175 g

Sources & evidence

ORD record
ord-8a092ab4f56b46c38ee723a56ade3862
Source dataset
uspto-grants-1987_11
Patent number
US04709048

Reaction notes

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