Water → HCID 21276497, compound

HRID 1381691Notes

Reaction equation

HRID 1381691 reaction equation
[OH:1][CH2:2][C:3]1([CH3:12])[C:7]2(OCC[O:8]2)[CH2:6][S:5][CH2:4]1.C1COCC1.O>C(O)(=O)C>[OH:1][CH2:2][C:3]1([CH3:12])[CH2:4][S:5][CH2:6][C:7]1=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 21276502HCID 21276502, compound

Product 1

HCID 21276497HCID 21276497, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 0.23 g (1.2 mmol) of product from Step C, 4.8 ml THF, 4.8 ml H2O, and 7.2 ml acetic acid was heated at 70° C. for 96 hours. The cooled mixture was concentrated and the residue was dissolved in ethyl acetate (75 ml), washed with saturated sodium bicarbonate solution (15 ml), and brine, dried, filtered, and concentrated to give 0.19 g of an oil. The oil was flash chromatographed on silica gel eluting with chloroform to give 0.09 g (50%) of product as an oil; NMR (deuteriochloroform): δ 3.79 (dd, 1H), 3.58 (dd, 1H), 3.33 (d, 2H), 3.30 (d, 1H), 2.71 (d, 1H), 1.98 (t, 1H, --OH), 1.22 (S, 3H).

Workup

  1. concentrationThe cooled mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate (75 ml)
  3. washwashed with saturated sodium bicarbonate solution (15 ml), and brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2104d550ea8c44689f70f1c141ed1401
Source dataset
uspto-grants-1989_02
Patent number
US04803286

Reaction notes

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