Ethanethiol → HCID 11760840, compound

HRID 128914Notes

Reaction equation

HRID 128914 reaction equation
C(OO)(=O)C.O[C@@H:7]1[O:26][C@H:25]([CH2:27][OH:28])[C@@H:12]([O:13][C@@H:14]2[O:22][C@H:21]([CH2:23][OH:24])[C@H:19]([OH:20])[C@H:17]([OH:18])[C@H:15]2[OH:16])[C@H:10]([OH:11])[C@H:8]1[OH:9].[CH2:29]([SH:31])[CH3:30].B(F)(F)F.CCOCC.[OH-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(Cl)Cl>[C@@H:14]1([O:13][C@@H:12]2[C@@H:25]([CH2:27][OH:28])[O:26][C@@H:7]([S:31][CH2:29][CH3:30])[C@H:8]([OH:9])[C@H:10]2[OH:11])[O:22][C@H:21]([CH2:23][OH:24])[C@H:19]([OH:20])[C@H:17]([OH:18])[C@H:15]1[OH:16]

Participants

7

Reactant 4

HCID 6343EthanethiolHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 131719198HCID 131719198, compound

Product 1

HCID 11760840HCID 11760840, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584019Toluene ethylacetateSolvent

Procedure

To a mixture of β-lactose peracetate (50 g), ethanethiol (6.9 g, 822 ml) and 200 ml dry CH2Cl2 was added BF3 /Et2O (8.5 g, 7.3 ml) at RT. After 2 hours, TLC (toluene/ethyl acetate 2/3) showed no more reaction. The mixture was shaken with ca 500 ml 1M NaOH. The organic layer was directly evaporated and taken up in methanol (150 ml), then NaOMe in methanol (10 ml, 0.5M) was added and the mixture was stirred overnight at RT. The TLC (ethyl acetate/acetic acid/methanol/water 12/3/3/3) yields an Rf 0.41. The reaction mixture was neutralized with Dowex (50w×8, H+) filtered and concentrated The residue was recrystallized from ethanol (300 ml). Yield 16.4 g, 56%, mp 191°-192° C.

Workup

  1. customno more reaction
  2. customThe organic layer was directly evaporated
  3. additionNaOMe in methanol (10 ml, 0.5M) was added
  4. customThe TLC (ethyl acetate/acetic acid/methanol/water 12/3/3/3) yields an Rf 0.41
  5. filtrationfiltered
  6. concentrationconcentrated The residue
  7. customwas recrystallized from ethanol (300 ml)

Sources & evidence

ORD record
ord-c86389b304604f4a81ff78a303600601
Source dataset
uspto-grants-1995_11
Patent number
US05466681

Reaction notes

Loading…