Hydrochloric Acid → (+)-trans-1-t-Butyldimethylsilyloxymethyl-4-oxo-2-phenylcyclopentane

HRID 2303679Notes

Reaction equation

HRID 2303679 reaction equation
[OH:1][CH2:2][C@H:3]1[C@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][C:5](=[O:14])[CH2:4]1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].CCN(C(C)C)C(C)C.Cl>C(Cl)Cl>[Si:15]([O:1][CH2:2][C@H:3]1[C@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][C:5](=[O:14])[CH2:4]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 53754795(+)-trans-3-Hydroxymethyl-4-phenylcyclopentan-1-one

Product 1

HCID 18686192(+)-trans-1-t-Butyldimethylsilyloxymethyl-4-oxo-2-phenylcyclopentaneYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (+−)-trans-3-hydroxymethyl-4-phenylcyclopentan-1-one from Step C (5.0 g, 24 mmol) in methylene chloride (100 mL) was added t-butyldimethylsilyl chloride (11.5 g, 48 mmol) and DIPEA (8.6 mL, 48 mmol). The reaction mixture was stirred at rt for 16 h, poured into dilute aq. HCl and extracted twice with ether. The organic layers were washed with brine, dried over sodium sulfate, combined and concentrated. The residue was purified by FC (5% ethyl acetate in hexanes) to afford the title compound (6.5 g) as a oil.

Workup

  1. extractionextracted twice with ether
  2. washThe organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by FC (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6778ee667c5b4844806e5c340eab6b71
Source dataset
uspto-grants-2002_08
Patent number
US06432981B1

Reaction notes

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