Sulfuric Acid → Estra-16-en-3beta-ol

HRID 369702Notes

Reaction equation

HRID 369702 reaction equation
[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C:7](=[CH:8][CH2:9][C:10]4[CH:11]=[C:12]([OH:19])[CH:13]=[CH:14][C:15]=43)[C@@H:6]1[CH2:5][CH2:4][CH2:3]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].OS(O)(=O)=O>CCOCC>[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH2:8][CH2:9][CH:10]4[C@@H:15]3[CH2:14][CH2:13][C@H:12]([OH:19])[CH2:11]4)[C@@H:6]1[CH2:5][CH:4]=[CH:3]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 15870996Estra-1,3,5(10),7-tetraen-3-olHCID 21226445Aluminium lithium hydride

Product 1

HCID 22849347Estra-16-en-3beta-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

This synthesis is depicted in FIG. 11. A solution of the ketone 10 (800 mg, 3.10 mmol) in dry ether (5 ml) was added dropwise at RT. to a slurry of LiAlH4 (38 mg, 1 mmol) in ether (3 ml) (e). After 1 h, the mixture was hydrolyzed with 10% aq. H2SO4. After workup (ether), the crude product (802 mg, 9:1-mixture of 12 and 11) was chromatographed on silica gel with CH2Cl2. A small fraction of 11 (70 mg) was eluted first, followed by the main fraction of 12 (705 mg, 87%). M.p. 113-115°, [a]--+36.3° (C=1.0).--IR. (CHCl3): 3640 m, 3500 br., 1585 w.--1H-NMR. (90 MHz): 0.78 (s, 3 H); 3.60 (m, w1/2 ≈(m, 20, 1 H); 5.71 (m, 1 H), 5.87 (m, 1 H).

Workup

  1. customAfter workup (ether), the crude product (802 mg, 9:1-mixture of 12 and 11) was chromatographed on silica gel with CH2Cl2
  2. washA small fraction of 11 (70 mg) was eluted first
  3. custom+36.3° (C=1.0)

Sources & evidence

ORD record
ord-4ad0251d080047bda4b6a412c1185d9b
Source dataset
uspto-grants-2000_10
Patent number
US06140316

Reaction notes

Loading…