Trityl chloride → HCID 2733809, compound

HRID 1828687Notes

Reaction equation

HRID 1828687 reaction equation
[OH:1][CH2:2][C@H:3]1[O:7][C:6](=[O:8])[CH2:5][CH2:4]1.C(N(CC)CC)C.[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:16]([O:1][CH2:2][C@H:3]1[O:7][C:6](=[O:8])[CH2:5][CH2:4]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 2733813(S)-(+)-gamma-Hydroxymethyl-gamma-butyrolactone

Product 1

HCID 2733809HCID 2733809, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The product from step 2 was dissolved in dry CH2Cl2 and the solution was cooled to 0° C. Triethylamine (1.5 molar equiv) was added. After 10 min, trityl chloride (1.1 molar equiv) followed by DMAP (0.2 molar equiv) were added and stirred over night at room temperature. The reaction was then quenched with saturated NH4Cl solution, the organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with water, brine, dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography afforded (5S)-5-(trityloxymethyl)-2-oxo-tetrahydrofuran in 76% yield.

Workup

  1. additionwere added
  2. customThe reaction was then quenched with saturated NH4Cl solution
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic extracts were washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customPurification by column chromatography

Sources & evidence

ORD record
ord-18d8181c8f994ee582ba364f36310a2b
Source dataset
uspto-grants-2006_06
Patent number
US07060678B2

Reaction notes

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