Carbon Tetrachloride → HCID 54302749, compound

HRID 486722Notes

Reaction equation

HRID 486722 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[S:12][C@@H:11]([CH2:13]O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:35].CCCCCC>C(OCC)C>[C:1]([O:5][C:6]([C@@H:8]1[S:12][C@@H:11]([CH2:13][Cl:35])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8058HexaneHCID 11776TriphenylphosphineHCID 53812277HCID 53812277, compound

Product 1

HCID 54302749HCID 54302749, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of trans-5-tert-butoxycarbonyl-2-hydroxymethyltetrahydrothiophene (compound No. 1-5, 5.0 g) in anhydrous diethylether (80 ml), triphenylphosphine (9.7 g) and carbon tetrachloride (5.7 g) are added under nitrogen atmosphere and the mixture is stirred for 2 hours at room temperature. n-Hexane (200 ml) is added to the mixture and filtrated. The filtrate is concentrated in vacuo. The oily residue is purified by a silica gel column chromatography to give trans-5-tert-butoxycarbonyl-2-chloromethyltetrahydrothiophene.

Workup

  1. filtrationfiltrated
  2. concentrationThe filtrate is concentrated in vacuo
  3. customThe oily residue is purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-a2c73038fbff4c47a1eeea4520f144be
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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