Propylene Oxide → 3-((s)-2-Hydroxypropylthio)phenylboronic acid

HRID 2098645Notes

Reaction equation

HRID 2098645 reaction equation
[CH2:1]1[O:4][CH:2]1[CH3:3].[SH:5][C:6]1[CH:7]=[C:8]([B:12]([OH:14])[OH:13])[CH:9]=[CH:10][CH:11]=1.[O-2].[Al+3].[O-2].[O-2].[Al+3]>C(OCC)C>[OH:4][C@@H:2]([CH3:3])[CH2:1][S:5][C:6]1[CH:7]=[C:8]([B:12]([OH:14])[OH:13])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 27739223-Mercaptophenylboronic AcidHCID 9989226Alumina

Product 1

HCID 671904283-((s)-2-Hydroxypropylthio)phenylboronic acidYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

S-(−) Propylene oxide (152 μL) was added to a mixture of 500 mg of 3-mercaptophenylboronic acid and aluminum oxide (˜30 eq, neutral, activated, ˜150 mesh) in diethyl ether at room temperature. The reaction was monitored by LC/MS until complete. The reaction mixture was evaporated, and then added 1N HCl. The resulting mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over MgSO4, filtered and evaporated to give 3-((S)-2-hydroxypropylthio)phenylboronic acid (414 mg, 90%). The crude product was directly used for next step reaction without purification.

Workup

  1. customThe reaction mixture was evaporated
  2. additionadded 1N HCl
  3. extractionThe resulting mixture was extracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e099467d23a9471a9a2c077cb5b45093
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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