Cyclopentanol → (+/-)-Ethyl 4-[4-(cyclopentyloxy)phenyl]-2-methyl-2-(methylsulfonyl)butanoate

HRID 533565Notes

Reaction equation

HRID 533565 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH:13]1([OH:18])[CH2:17][CH2:16][CH2:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][C:47]([CH3:57])([S:53]([CH3:56])(=[O:55])=[O:54])[C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:41][CH:40]=1>C1COCC1>[CH:13]1([O:18][C:39]2[CH:40]=[CH:41][C:42]([CH2:45][CH2:46][C:47]([CH3:57])([S:53]([CH3:56])(=[O:55])=[O:54])[C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:43][CH:44]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 56951126(+/-)-Ethyl 4-(4-hydroxyphenyl)-2-methyl-2-(methylsulfonyl)butanoate

Product 1

HCID 86668780(+/-)-Ethyl 4-[4-(cyclopentyloxy)phenyl]-2-methyl-2-(methylsulfonyl)butanoateYield 81.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (40%, 220 uL, 0.48 mmol) was added to a solution of cyclopentanol (30.2 uL, 0.333 mmol), triphenylphosphine (120 mg. 0.456 mmol), and (+/−)-ethyl 4-(4-hydroxyphenyl)-2-methyl-2-(methylsulfonyl)butanoate (120 mg, 0.40 mmol) in THF (3 mL) at 0° C. under nitrogen. The reaction was allowed to warm to rt and was stirred overnight. The reaction was quenched with water (20 mL) and extracted with ethyl acetate (3×30 mL). The combined organics were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified via column chromatography using an Analogiz SF10-8 g using EtOAc in Heptane (10-50%) to afford the title compound as a clear oil (100 mg, 67.8%). LC-MS m/z 369.4 (M+1).

Workup

  1. customThe reaction was quenched with water (20 mL)
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified via column chromatography

Sources & evidence

ORD record
ord-555f920000ff4ff7882cd6da2d92ecc4
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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