Dimethyl Sulfoxide → HCID 67485750, compound

HRID 1430641Notes

Reaction equation

HRID 1430641 reaction equation
C1NC2N([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C=NC=2C(=O)N=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1COCC1.[CH:44]1([CH2:49][O:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[OH:57])[CH2:48][CH2:47][CH2:46][CH2:45]1.[CH2:58]([O:60][C:61](=[O:66])[C:62](Br)([CH3:64])[CH3:63])[CH3:59].CS(C)=O>O>[CH2:58]([O:60][C:61](=[O:66])[C:62]([O:57][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=1[O:50][CH2:49][CH:44]1[CH2:45][CH2:46][CH2:47][CH2:48]1)([CH3:64])[CH3:63])[CH3:59]

Participants

8

Reactant 6

HCID 679Dimethyl SulfoxideHCID 8028TetrahydrofuranHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 11776TriphenylphosphineHCID 61343388HCID 61343388, compoundHCID 178518212HCID 178518212, compound

Product 1

HCID 67485750HCID 67485750, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of catacol (0.5 g, 4.54 mmol), triphenylphosphine (1.79 g, 6.8 mmol) and cyclopenylmethanol (0.68 g, 6.8 mmol) in THF (5 ml) DIAD (1.37 g, 6.8 mmol) is added drop wise over a period of 10-15 min at 0° C. The reaction mixture stirred at r.t. for 18 h, quenched with brine (5 ml), extracted in EtOAc (2×20 ml), and dried over Na2SO4. Solvent was evaporated under reduced pressure and crude product. To a solution of 2-Cyclopentylmethoxy-phenol (0.1 g, 0.52 mmol) and 2-bromoisobutyrate ethyl ester (0.15 g, 0.78 mmol) in DMSO (2 ml) Cs2CO3 (0.25 g, 0.78 mmol) was added and heated at 60° C. for 4 h. The reaction mixture was cooled to r.t. and poured on 10 ml of water, extracted in EtOAc (2×20 ml) dried over Na2SO4. Solvent was removed under reduced pressure to yield 2-(2-Cyclopentylmethoxy-phenoxy)-2-methyl-propionic acid ethyl ester (0.1 g, 63%) which was hydrolysed to give 2-(2-Cyclopentylmethoxy-phenoxy)-2-methyl-propionic acid using method Typical Example (A1-II).

Workup

  1. customquenched with brine (5 ml)
  2. extractionextracted in EtOAc (2×20 ml)
  3. dry with materialdried over Na2SO4
  4. customSolvent was evaporated under reduced pressure and crude product
  5. temperatureheated at 60° C. for 4 h
  6. temperatureThe reaction mixture was cooled to r.t.
  7. extractionextracted in EtOAc (2×20 ml)
  8. dry with materialdried over Na2SO4
  9. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-eba4edb5059d4969aca06712177f75ac
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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